Stereoselective Synthesis of Cyclohexane Derivatives: Tandem Lithium Iodide Mediated Intramolecular Conjugate Addition of Thiols to α,β-Bisenones

Minseok Jeon; Chaeyoung Yun; SungYong Seo

doi:10.1055/a-1754-7424

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(12): 2865-2875
DOI: 10.1055/a-1754-7424

paper

Stereoselective Synthesis of Cyclohexane Derivatives: Tandem Lithium Iodide Mediated Intramolecular Conjugate Addition of Thiols to α,β-Bisenones

Minseok Jeon

^aDepartment of Chemistry, Pukyong National University, Busan, 48513, Republic of Korea

,

Chaeyoung Yun

^bDepartment of Smart Green Technology Engineering, Pukyong National University, Busan, 48513, Republic of Korea

,

SungYong Seo ∗

^aDepartment of Chemistry, Pukyong National University, Busan, 48513, Republic of Korea

^bDepartment of Smart Green Technology Engineering, Pukyong National University, Busan, 48513, Republic of Korea

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Abstract

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Abstract

A tandem intramolecular conjugate addition reaction was conducted with α,β-bisenones as selected Michael acceptors which were converted into 1,2,3-trisubstituted six-membered rings in the presence of activated sulfur nucleophiles. The products were obtained in good to excellent yields (maximum yield: 99%). Various substituted α,β-bisenones and sulfur nucleophiles were examined to understand the substrate scope of the reaction. Only one diastereomer was isolated, as lithium iodide mediated enolate trapping reactions improve the stereoselectivity of reactions involving 1,2,3-trisubstituted cyclohexanes.

Key words

stereoselectivity - tandem conjugate addition - lithium iodide - α,β-bisenones - thiols

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References

For reviews, see:

1a Tietze LF. Chem. Rev. 1996; 96: 115
1b Denmark SE, Thorarensen A. Chem. Rev. 1996; 96: 137
1c Parsons PJ, Penkett CS, Shell AJ. Chem. Rev. 1996; 96: 195
1d Sibi MP, Manyem S. Tetrahedron 2000; 56: 8033
1e Krause N, Hoffmann-Roder A. Synthesis 2001; 171
1f Fagnou K, Lautens M. Chem. Rev. 2003; 103: 169
1g Guo H.-C, Ma J.-A. Angew. Chem. Int. Ed. 2006; 45: 354
1h Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
1i Chanda T, Zhao JC.-G. Adv. Synth. Catal. 2018; 360: 2

For reviews, see:

2a Jerphagnon T, Pizzuti MG, Minnaard AJ, Feringa BL. Chem. Soc. Rev. 2009; 38: 1039
2b Csákÿa AG, Herrán G, Murcia MC. Chem. Soc. Rev. 2010; 39: 4080
2c Dong N, Zhang Z, Xue X, Li X, Cheng J. Angew. Chem. Int. Ed. 2016; 55: 1460
2d Sekino E, Kumamoto T, Tanaka T, Ikeda T, Ishikawa T. J. Org. Chem. 2004; 69: 2760
2e Fu N, Zhang L, Luo S, Cheng J. Org. Lett. 2014; 16: 4626

3a Liu Y, Zhu J, Qian J, Jiang B, Xu Z. J. Org. Chem. 2011; 76: 9096
3b Hagare AK, Datrange LS, Vyas D, Bhuniya D, Reddy DS. Tetrahedron Lett. 2010; 51: 5291
3c Davies SG, Mujtaba N, Roberts PM, Smith AD, Thomson JE. Org. Lett. 2009; 11: 1959

4a Meng D, Chen W, Zhao W. J. Nat. Prod. 2007; 70: 824
4b Sabarre A, Love J. Org. Lett. 2008; 10: 3941
4c Yus M, Gutiérrez A, Foubelo F. Tetrahedron 2001; 57: 4411
4d Metzner P, Thuillier A. Sulfur Reagents in Organic Synthesis . Academic Press; San Diego: 1994
4e Belen’kii LI. Chemistry of Organosulfur Compounds . Ellis Horwood; New York: 1990
4f Konkolewicz D, Gray-Weale A, Perrier S. J. Am. Chem. Soc. 2009; 131: 18075
4g Roncali J. Chem. Rev. 1992; 92: 711
4h Feng Z.-N, Luo J.-Y, Zhang Y, Du G.-F, He L. Org. Biomol. Chem. 2019; 17: 4700
4i Chavan SP, Subbarao YT, Chittiboyina AG, Sivappa R, Suresh CG. Tetrahedron: Asymmetry 2001; 12: 1101
4j Gigant N, Drège E, Retailleau P, Joseph D. Chem. Eur. J. 2015; 21: 15544

5 Gulino V, Brighi M, Dematteis EM, Murgia F, Nervi C, Černy R, Baricco M. Chem. Mater. 2019; 31: 5133

6a Loupy A, Tchoubar B. Salt Effects in Organic and Organometallic Chemistry. VCH; Weinheim: 1992
6b Manna S, Falck JR, Mioskowski C. Synth. Commun. 1985; 15: 663

7 Zewge D, King A, Weissman S, Tschaen D. Tetrahedron Lett. 2004; 45: 3729

8a Kawai D, Kawasumi K, Miyahara T, Hirashita T, Araki S. Synlett 2008; 2977
8b Kawai D, Kawasumi K, Miyahara T, Hirashita T, Araki S. Tetrahedron 2009; 65: 10390
8c Yoshimura A, Koski SR, Kastern BJ, Fuchs JM, Jones TN, Yusubova RY, Nemykin VN, Zhdankin VV. Chem. Eur. J. 2014; 20: 5895

9a Miyabe H, Yamaoka Y, Naito T, Takemoto Y. J. Org. Chem. 2004; 69: 1415
9b Park SH, Yoon HK, Lee HW. Bull. Korean Chem. Soc. 2006; 27: 1519

10 Hirner S, Somfai P. Synlett 2005; 3099

11a Yatagai H, Yamamoto Y, Maruyama K. Chem. Lett. 1980; 669
11b Yanada R, Obika S, Kobayashi Y, Inokuma T, Oyama M, Yanada K, Takemoto Y. Adv. Synth. Catal. 2005; 347: 1632

12a Bonini C, Giuliano C, Righi G, Rossi L. Synth. Commun. 1992; 22: 1863
12b Federici C, Righi G, Rossi L. Tetrahedron Lett. 1994; 35: 797
12c Bonini C, Federici C, Rossi L, Righi G. J. Org. Chem. 1995; 60: 4803
12d Infante I, Bonini C, Lelj F, Righi G. J. Org. Chem. 2003; 68: 3773

13a Too PC, Chan GH, Tnay YL, Hirao H, Chiba S. Angew. Chem. Int. Ed. 2016; 55: 3719
13b Hong Z, Ong DY, Muduli SK, Too PC, Chan GH, Tnay YL, Chiba S, Nishiyama Y, Hirao H, Soo HS. Chem. Eur. J. 2016; 22: 7108

14 Ong DY, Tejo C, Xu K, Hirao H, Chiba S. Angew. Chem. Int. Ed. 2017; 56: 1840
15 Kaga A, Hayashi H, Hakamata H, Oi M, Uchiyama M, Takita R, Chiba S. Angew. Chem. Int. Ed. 2017; 56: 11807
16 Huang Y, Chan GH, Chiba S. Angew. Chem. Int. Ed. 2017; 56: 6544

17a Marques MV, Sá MM. J. Org. Chem. 2014; 79: 4650
17b Tokuda O, Aikawa T, Ikemoto T, Kuriomoto I. Tetrahedron Lett. 2010; 51: 2832

18 Thirupathaiah B, Seo S. Chem. Commun. 2015; 51: 4216

19a Wang L.-C, Luis AL, Agapiou K, Jang H.-Y, Krische MJ. J. Am. Chem. Soc. 2002; 124: 2402
19b Reynolds TE, Binkley MS, Scheidt KA. Org. Lett. 2008; 10: 2449
19c Wang CE, Dermenci A, Miller SJ. Tetrahedron 2009; 65: 4069
19d Aroyan CE, Dermenci A, Miller SJ. J. Org. Chem. 2010; 75: 5784
19e Osuna S, Dermenci A, Miller SJ, Houk KN. Chem. Eur. J. 2013; 19: 14245
19f Brown PM, Käppel N, Murphy PJ, Coles SJ, Hursthouse MB. Tetrahedron 2007; 63: 1100

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