Synthesis of sp3-Enriched β-Fluoro Sulfonyl Chlorides

Rustam Gurbanov; Andriy Sokolov; Sergey Golovach; Kostiantyn Melnykov; Alexey V. Dobrydnev; Oleksandr O. Grygorenko

doi:10.1055/s-0040-1706101

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(10): 1771-1784
DOI: 10.1055/s-0040-1706101

paper

Synthesis of sp³-Enriched β-Fluoro Sulfonyl Chlorides

Rustam Gurbanov

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

,

Andriy Sokolov

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Sergey Golovach

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

,

Kostiantyn Melnykov

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Alexey V. Dobrydnev

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Oleksandr O. Grygorenko ∗

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A three-step approach to the synthesis of sp³-enriched β-fluoro sulfonyl chlorides starting from alkenes is reported. The method was successfully applied to a wide range of acyclic and cyclic substrates, bearing either an exocyclic or an endocyclic double bond. The procedure worked with a wide range of substrates and tolerated a number of functional and protecting groups. Moreover, the target cyclic compounds were obtained as single cis diastereomers on a multigram scale. The title compounds are promising building blocks for drug discovery that can be used to obtain sp³-enriched β-fluoro and α,β-unsaturated sulfonamides.

Key words

organosulfur compounds - organofluorine compounds - oxidation - sulfonyl chlorides - building blocks

Volltext

Referenzen

References

1a The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science. Greenberg A, Breneman CM, Liebman JF. John Wiley & Sons, Inc; New York: 2000
1b Brameld KA, Kuhn B, Reuter DC, Stahl M. J. Chem. Inf. Model. 2008; 48: 1

2 Koeplinger KA, Zhao Z, Peterson T, Leone JW, Schwende FS, Heinrikson RL, Tomasselli AG. Drug Metab. Dispos. 1999; 27: 986

3a Ajeet, Mishra AK, Kumar A. Am. J. Pharmacol. Sci. 2015; 3: 18
3b The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine. Lesch JE. Oxford University Press; New York: 2007
3c Domagk G. Dtsch. Med. Wochenschr. 1935; 61: 250
3d Drews J. Science 2000; 287: 1960
3e Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Curr. Med. Chem. 2003; 10: 925

4 Raju TN. K. Lancet 1999; 353: 681
5 DrugBank (accessed Jan 3 2020). www.drugbank.ca.

6a Tolmachova KA, Moroz YS, Konovets A, Platonov MO, Vasylchenko OV, Borysko P, Zozulya S, Gryniukova A, Bogolubsky AV, Pipko S, Mykhailiuk PK, Brovarets VS, Grygorenko OO. ACS Comb. Sci. 2018; 20: 672
6b Mykhalchuk VL, Yarmolchuk VS, Doroschuk RO, Tolmachev AA, Grygorenko OO. Eur. J. Org. Chem. 2018; 2870
6c Sokolov A, Golovach S, Kozlinsky I, Dolia K, Tolmachev AA, Kuchkovska Y, Grygorenko OO. Synthesis 2019; 51: 848
6d Cherepakha AYu, Stepannikova KO, Vashchenko BV, Gorichko MV, Tolmachev AA, Grygorenko OO. Eur. J. Org. Chem. 2018; 6682
6e Yang Z, Zhou B, Xu J. Synthesis 2014; 46: 225
6f Yang Z, Zheng Y, Xu J. Synlett 2013; 24: 2165
6g Yang Z, Xu J. Synthesis 2013; 45: 1675

7a Wolkenberg SE, Zhao Z, Wisnoski DD, Leister WH, O’Brien J, Lemaire W, Williams DL, Jacobson MA, Sur C, Kinney GG, Pettibone DJ, Tiller PR, Smith S, Gibson C, Ma BK, Polsky-Fisher SL, Lindsley CW, Hartman GD. Bioorg. Med. Chem. Lett. 2009; 19: 1492
7b Melngaile R, Sperga A, Baldridge KK, Veliks J. Org. Lett. 2019; 21: 7174

8a Saunders BC, Stacey GJ, Wilding IG. E. J. Chem. Soc. 1949; 773
8b Howell WC, Millington JE, Pattison FL. M. J. Am. Chem. Soc. 1956; 78: 3843
8c Bunyagidj C, Piotrowska H, Aldridge MH. J. Chem. Eng. Data 1981; 26: 344

9a Wang L, Pratt JK, McDaniel KF, Dai Y, Fidanze SD, Hasvold L, Holms JH, Kati WM, Liu D, Mantei RA, McClellan WJ, Sheppard GS, Wada CK. US 2014162971, 2014
9b Mao Z, Ma D, Ge Y, Ren X, Li Y. CN 105622469, 2016
9c Dai W, Xi N, Li M, Zhang T, Li X, Hu H, Chen W, Wang T, Liu J. WO 201748675, 2017
9d Braun M.-G, Gibbons P, Lee W, Ly C, Rudolph J, Schwarz J, Ashkenazi A, Fu L, Lai T, Wang F, Beveridge R, Zhao L. WO 2018166528, 2018

10a Liu S, Zeng X, Xu B. Org. Chem. Front. 2019; 7: 119
10b Haufe G, Alvernhe G, Anker D, Laurent A, Saluzzo C. Tetrahedron Lett. 1988; 29: 2311

11a Lübke M, Skupin R, Haufe G. J. Fluorine Chem. 2000; 102: 125
11b Moens M, D’Hooghe M, De Kimpe N. Tetrahedron Lett. 2013; 54: 6110
11c Verniest G, Piron K, Van Hende E, Thuring JW, MacDonald G, Deroose F, De Kimpe N. Org. Biomol. Chem. 2010; 8: 2509
11d Camps F, Chamorro E, Gasol V, Guerrero A. J. Org. Chem. 1989; 54: 4294
11e Hashimoto T, Prakash GK. S, Shih JG, Olah GA. J. Org. Chem. 1987; 52: 931
11f Shimizu M, Nakahara Y, Yoshioka H. J. Chem. Soc., Chem. Commun. 1989; 1881
11g Olah GA, Bollinger JM. J. Am. Chem. Soc. 1967; 89: 4744
11h Olah GA, Li X.-Y, Wang Q, Prakash GK. S. Synthesis 1993; 693
11i Alvernhe G, Laurent A, Haufe G. Synthesis 1987; 562

12 Cope AC, Martin MM, McKervey MA. Q. Rev., Chem. Soc. 1966; 20: 119
13 Nadin A, Hattotuwagama C, Churcher I. Angew. Chem. Int. Ed. 2012; 51: 1114
14 Armarego WL. F, Chai C. Purification of Laboratory Chemicals, 5th ed. Elsevier; Oxford: 2003
15 Schmid GH, Strukelj M, Dalipi S, Ryan MD. J. Org. Chem. 1987; 52: 2403

16a Kim J, Zhang Y, Ran C, Sayre LM. Bioorg. Med. Chem. 2006; 14: 1444
16b Delogu G, Faedda G, Gladiali S. J. Organomet. Chem. 1984; 268: 167
16c Stille JK, Becker Y. J. Org. Chem. 1980; 45: 2139

17a Thumme RP, Nutaku W. J. Org. Chem. 1978; 43: 3170
17b Conner ML, Brown MK. J. Org. Chem. 2016; 81: 8050
17c Olah GA, Reddy VP, Surya Prakash GK. Synthesis 1991; 29
17d Green SA, Vásquez-Céspedes S, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 11317
17e Liu X, Zhang W, Wang Y, Zhang ZX, Jiao L, Liu Q. J. Am. Chem. Soc. 2018; 140: 6873
17f Matos JL. M, Vásquez-Céspedes S, Gu J, Oguma T, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 16976

Zusatzmaterial

Supporting Information