Advances in 2-(Alkoxycarbonyl)allylboration
of Carbonyl Compounds and Other Direct Methods for the Preparation
of α-Exo-Alkylidene γ-Lactones

Tim G. Elford; Dennis G. Hall

doi:10.1055/s-0029-1218664

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Synthesis 2010(6): 893-907
DOI: 10.1055/s-0029-1218664

REVIEW

Advances in 2-(Alkoxycarbonyl)allylboration of Carbonyl Compounds and Other Direct Methods for the Preparation of α-Exo-Alkylidene γ-Lactones

Tim G. Elford, Dennis G. Hall*
Department of Chemistry, University of Alberta, W5-07 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada
Fax: +1(780)4928231; e-Mail: dennis.hall@ualberta.ca;

Further Information

Publication History

Received 14 October 2009
Publication Date:
05 February 2010 (online)

Abstract
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Abstract

Reagents and methodologies allowing for direct preparation of α-exo-alkylidene γ-lactones are of great interest because of the multiple biological properties demonstrated by these natural and unnatural compounds. Relatively few simple and direct methods are available for the preparation of these important compounds, and these methods along with their applications in target-oriented and diversity-oriented synthesis are covered in this review focusing on the most recent advances in the literature.

1 Introduction

1.1 Importance of α-Exo-Methylene and α-Exo-Alkylidene γ-Lactones

1.2 Overview of Indirect Preparative Methods

2 Direct Preparative Methods by Additions of 2-(Alkoxycarbonyl)allylmetal Reagents to Aldehydes and Ketones

2.1 Thermal Additions of 2-(Alkoxycarbonyl)allyl Boronates

2.2 Lewis Acid Catalyzed Additions of 2-(Alkoxycarbonyl)allyl Boronates

2.3 Brønsted Acid Catalyzed Additions of 2-(Alkoxycarbonyl)allyl Boronates

2.4 Preparation of Libraries of α-Exo-Methylene γ-Lactones and Their Functionalization into α-Exo-Alkylidene γ-Lactones

3 Additions of Other 2-(Alkoxycarbonyl)allylmetal Reagents

4 Barbier-Type Additions with 2-(Alkoxycarbonyl)allyl Halides

5 Other Direct Methods

6 Conclusion

Key words

allylations - boron - catalysis - lactones - natural products

References

1 Hoffmann HMR. Rabe J. Angew. Chem., Int. Ed. Engl. 1985, 24: 94

Crossref Google Scholar
2 Konaklieva MI. Plotkin BJ. Mini Rev. Med. Chem. 2005, 5: 73

Crossref PubMed Google Scholar
3a Janecki T. Blaszczyk E. Studzian K. Janecka A. Krajewska U. Rózalski M. J. Med. Chem. 2005, 48: 3216

Google Scholar
3b Rózalski M. Krajewska U. Panczyk M. Mirowski M. Rózalska B. Wasek T. Janecki T. Eur. J. Med. Chem. 2007, 42: 248

Google Scholar
3c Albrecht A. Koszuk JF. Modranka J. Rózalski M. Krajewska U. Janecka A. Studzian K. Janecki T. Bioorg. Med. Chem. 2008, 16: 4872

Google Scholar
4 Zhangabylov NS. Dederer LY. Gorbacheva LB. Vasil’eva SV. Terekhov AS. Adekenov SM. Pharm. Chem. J. 2004, 38: 651

Crossref Google Scholar
5 Bernardi A. Beretta MG. Colombo L. Gennari C. Poli G. Scolastico C. J. Org. Chem. 1985, 50: 4442

Crossref Google Scholar
6 Edwards MG. Kenworthy MN. Kitson RRA. Scott MS. Taylor RJK. Angew. Chem. Int. Ed. 2008, 47: 1935

Crossref PubMed Google Scholar
7a Haaima G. Weavers RT. Tetrahedron Lett. 1988, 29: 1085

Google Scholar
7b Haaima G. Lynch M.-J. Routledge A. Weavers RT. Tetrahedron 1991, 47: 5203

Google Scholar
8a Biel M. Kretsovali A. Karatzali E. Papamatheakis J. Giannis A. Angew. Chem. Int. Ed. 2004, 43: 3974

Google Scholar
8b Hughes MA. McFadden JM. Townsend CA. Bioorg. Med. Chem. Lett. 2005, 15: 3857

Google Scholar
9 Nishiyama H. Yokoyama H. Narimatsu S. Itoh K. Tetrahedron Lett. 1982, 23: 1267

Crossref Google Scholar
10 Ramachandran PV. Garner G. Pratihar D. Org. Lett. 2007, 9: 4753

Crossref PubMed Google Scholar
11 Rauniyar V. Hall DG. J. Org. Chem. 2009, 74: 4236

Crossref PubMed Google Scholar
12 Semmelhack MF. Brickner SJ. J. Org. Chem. 1981, 46: 1723

Crossref Google Scholar
13a Denmark SE. Almstead NG. In Modern Carbonyl Chemistry Otera J. Wiley-VCH; Weinheim: 2000. Chap 10. p.299-402

Google Scholar
13b Chemler SR. Roush WR. In Modern Carbonyl Chemistry Otera J. Wiley-VCH; Weinheim: 2000. Chap 11. p.403-490

Google Scholar
14 Denmark SE. Fu J. Chem. Rev. 2003, 103: 2763

Crossref PubMed Google Scholar
15a Kennedy JWJ. Hall DG. In Boronic Acids Hall DG. Wiley-VCH; Weinheim: 2005. Chap 6. p.241-277

Google Scholar
15b Lachance H. Hall DG. Org. React. (New York) 2008, 73: 1-573

Google Scholar
16 Denmark SE. Weber EJ. Helv. Chim. Acta 1983, 66: 1655

Crossref Google Scholar
17a Hoffmann RW. Zeiss H.-J. Angew. Chem., Int. Ed. Engl. 1979, 18: 306

Google Scholar
17b Hoffmann RW. Zeiss H.-J. J. Org. Chem. 1981, 46: 1309

Google Scholar
18 Nyzam V. Belaud C. Villiéras J. Tetrahedron Lett. 1993, 34: 6899

Crossref Google Scholar
19 Chataigner I. Zammattio F. Lebreton J. Villiéras J. Tetrahedron 2008, 64: 2441

Crossref Google Scholar
20 Kennedy JWJ. Hall DG. J. Am. Chem. Soc. 2002, 124: 898

Crossref PubMed Google Scholar
21 Zhu N. Hall DG. J. Org. Chem. 2003, 68: 6066

Crossref PubMed Google Scholar
22 Ramachandran PV. Pratihar D. Biswas D. Srivastava A. Reddy MVR. Org. Lett. 2004, 6: 481

Crossref PubMed Google Scholar
23 Kabalka GW. Venkataiah B. Dong G. J. Org. Chem. 2004, 69: 5807

Crossref PubMed Google Scholar
24 Kennedy JWJ. Hall DG. J. Am. Chem. Soc. 2002, 124: 11586

Crossref PubMed Google Scholar
25 Ishiyama T. Ahiko T.-a. Miyaura N. J. Am. Chem. Soc. 2002, 124: 12414

Crossref PubMed Google Scholar
26 Kennedy JWJ. Hall DG. J. Org. Chem. 2004, 69: 4412

Crossref PubMed Google Scholar
27 Kabalka GW. Venkataiah B. Dong G. Tetrahedron Lett. 2005, 46: 4209

Crossref Google Scholar
28 Kabalka GW. Venkataiah B. Tetrahedron Lett. 2005, 46: 7325

Crossref Google Scholar
29 Ramachandran PV. Pratihar D. Biswas D. Org. Lett. 2006, 8: 3877

Crossref PubMed Google Scholar
30 Ramachandran PV. Pratihar D. Org. Lett. 2007, 9: 2087

Crossref PubMed Google Scholar
31 Kabalka GW. Venkataiah B. Chen C. Tetrahedron Lett. 2006, 47: 4187

Crossref Google Scholar
32 Rauniyar V. Hall DG. J. Am. Chem. Soc. 2004, 126: 4518

Crossref PubMed Google Scholar
33 Brown HC. Racherla US. Pellechia PJ. J. Org. Chem. 1990, 55: 1868

Crossref Google Scholar
34 Sakata K. Fujimoto H. J. Am. Chem. Soc. 2008, 130: 12519

Crossref PubMed Google Scholar
35 Yu S.-H. Ferguson MJ. McDonald R. Hall DG. J. Am. Chem. Soc. 2005, 127: 12808

Crossref Google Scholar
36a Carroll AR. Taylor WC. Aust. J. Chem. 1991, 44: 1615

Google Scholar
36b Carroll AR. Taylor WC. Aust. J. Chem. 1991, 44: 1705

Google Scholar
37a Hong S.-p. McIntosh MC. Org. Lett. 2002, 4: 19

Google Scholar
37b Hutchison JM. Hong S.-p. McIntosh MC. J. Org. Chem. 2004, 69: 4185

Google Scholar
37c Gurjar MK. Cherian J. Ramana CV. Org. Lett. 2004, 6: 317

Google Scholar
37d Coleman RS. Gurrala SR. Org. Lett. 2004, 6: 4025

Google Scholar
38 Elford TG. Yu SH. Arimura Y. Hall DG. J. Org. Chem. 2007, 72: 1276

Crossref PubMed Google Scholar
39 Le Lamer A.-C. Gouault N. David M. Boustie J. Uriac P. J. Comb. Chem. 2006, 8: 643

Crossref Google Scholar
40 Elford TG. Ulaczyk-Lesanko A. De Pascale G. Wright GD. Hall DG. J. Comb. Chem. 2009, 11: 155

Crossref PubMed Google Scholar
For example, see:
41a Heck RF. Nolley JP. J. Org. Chem. 1972, 37: 2320

Google Scholar
41b Perlmutter P. Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series 9 Pergamon; Oxford: 1992.

Google Scholar
41c Gibson SE. Keen SP. In Alkene Metathesis in Organic Synthesis Furstner A. Springer; Berlin/Heidelberg: 1999.

Google Scholar
41d Mortia K. Suzuki Z. Hirose H. Bull. Chem. Soc. Jpn. 1968, 41: 2815

Google Scholar
42a Raju R. Allen LJ. Le T. Taylor CD. Howell AR. Org. Lett. 2007, 9: 1699

Google Scholar
42b Moise J. Arseniyadis S. Cossy J. Org. Lett. 2007, 9: 1695

Google Scholar
For reviews see:
43a Heck RF. Acc. Chem. Res. 1979, 12: 146

Google Scholar
43b Crisp GT. Chem. Soc. Rev. 1998, 27: 427

Google Scholar
43c Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

Google Scholar
43d Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron 2001, 57: 7449

Google Scholar
43e van der Boom ME. Milstein D. Chem. Rev. 2003, 103: 1759

Google Scholar
43f Dounay AB. Overman LE. Chem. Rev. 2003, 103: 2945

Google Scholar
44 Du X. Suguro M. Hirabayashi K. Mori A. Org. Lett. 2001, 3: 3313

Crossref PubMed Google Scholar
45 Baldwin JE. Adlington RM. Sweeney JB. Tetrahedron Lett. 1986, 27: 5423

Crossref Google Scholar
46 Tanaka K. Yoda H. Isobe Y. Kaji A. J. Org. Chem. 1986, 51: 1856

Crossref Google Scholar
47 Masuyama Y. Nimura Y. Kurusu Y. Tetrahedron Lett. 1991, 32: 225

Crossref Google Scholar
48 Hosomi A. Hashimoto H. Sakurai H. Tetrahedron Lett. 1980, 21: 951

Crossref Google Scholar
49 Sidduri AR. Knochel P. J. Am. Chem. Soc. 1992, 114: 7579

Crossref Google Scholar
50 Öhler E. Reininger K. Schmidt U. Angew. Chem. Int. Ed. 1970, 6: 457

Google Scholar
51 Lambert F. Kirschleger B. Villiéras J. J. Organomet. Chem. 1991, 406: 71

Crossref Google Scholar
52 Mattes H. Benezra C. Tetrahedron Lett. 1985, 26: 5697

Crossref Google Scholar
53 Lee AS.-Y. Chang Y.-T. Wang S.-H. Chu S.-F. Tetrahedron Lett. 2002, 43: 8489

Crossref Google Scholar
54 Ding H. Zhang C. Wu X. Yang C. Zhang X. Ding J. Xie Y. Bioorg. Med. Chem. Lett. 2005, 15: 4799

Crossref PubMed Google Scholar
55 Choudhury PK. Foubelo F. Yus M. Tetrahedron Lett. 1998, 39: 3581

Crossref Google Scholar
56 Paquette LA. Méndez-Andino J. Tetrahedron Lett. 1999, 40: 4301

Crossref Google Scholar
57 Nokami J. Tamaoka T. Ogawa H. Wakabayashi S. Chem. Lett. 1986, 541

Crossref Google Scholar
58 Okuda Y. Nakatsukasa S. Oshima K. Nozaki H. Chem. Lett. 1985, 481

Crossref Google Scholar
59 González AG. Hernández Silva M. Padrón JI. León F. Reyes E. Álvarez-Mon M. Pivel JP. Quintana J. Estévez F. Bermejo J. J. Med. Chem. 2002, 45: 2358

Crossref PubMed Google Scholar
60 Fürstner A. Shi N. J. Am. Chem. Soc. 1996, 118: 2533

Google Scholar
61 Paira M. Banerjee B. Jana S. Mandal SK. Roy SC. Tetrahedron Lett. 2007, 48: 3205

Crossref Google Scholar
62 Lee K. Jackson JJ. Wiemer DF. J. Org. Chem. 1993, 58: 5967

Crossref Google Scholar
63 Trost BM. Corte JR. Gudiksen MS. Angew. Chem. Int. Ed. 1999, 38: 3662

Google Scholar
64 Gagnier SV. Larock RC. J. Org. Chem. 2000, 65: 1525

Crossref PubMed Google Scholar
65 Yong X. Li D. Zhang Z. Zhang X. J. Am. Chem. Soc. 2004, 126: 7601

Crossref PubMed Google Scholar
66 Lei A. He M. Zhang X. J. Am. Chem. Soc. 2002, 124: 8198

Google Scholar