Enantioselective Organocatalytic Approach to the Synthesis of α,α-Disubstituted Cyanosullfones

被引：28

作者：

Cid, M. Belen ^{[1
]}

Lopez-Cantarero, Jesus ^{[1
]}

Duce, Sara ^{[1
]}

Ruano, Jose Luis Garcia ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 01期

关键词：

QUATERNARY STEREOCENTERS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; CONSTRUCTION; ESTERS; ACIDS;

D O I：

10.1021/jo801968p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure cyano tert-alkyl sulfones have been obtained by organocatalytic enantioselective Michael addition of alpha-substituted cyanosulfones to vinyl ketones using cinchona alkaloids as catalysts. The best results were obtained for p-trifluorophenylsulfones by using VIII as catalyst in toluene at -40 degrees C. Reactions proved to be applicable for a variety of alpha,beta-unsaturated ketones. affording alpha,alpha-disubstituted cyanosulfones in excellent yields with er's up to 90:10.

引用

页码：431 / 434

页数：4

共 47 条

[1] Organocatalytic asymmetric conjugate additions
Almasi, Diana
Alonso, Diego A.
Najera, Carmen
[J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
[2] Asymmetric synthesis of α,β-epoxysulfones under phase-transfer catalyzed Darzens reaction
Arai, S
Ishida, T
Shioiri, T
[J]. TETRAHEDRON LETTERS, 1998, 39 (45) : 8299 - 8302
[3] Synthesis and structure-activity relationship of α-sulfonylhydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis
Aranapakam, V
Grosu, GT
Davis, JM
Hu, BH
Ellingboe, J
Baker, JL
Skotnicki, JS
Zask, A
DiJoseph, JF
Sung, A
Sharr, MA
Killar, LM
Walter, T
Jin, GX
Cowling, R
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (12) : 2361 - 2375
[4] A novel organocatalytic tool for the iminium activation of α,β-unsaturated ketones
Bartoli, Giuseppe
Melchiorre, Paolo
[J]. SYNLETT, 2008, (12) : 1759 - 1772
[5] Organocatalytic asymmetric deconjugative Michael additions
Bell, Mark
Frisch, Kim
Anker Jorgensen, Karl
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) : 5407 - 5410
[6] Organocatalytic enantioselective conjugate addition to alkynones
Bella, M
Jorgensen, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) : 5672 - 5673
[7] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[8] BERRY A, 2008, Patent No. 2008014199
[9] Synthesis of chiral catalyst modifiers by hydrosilylation of cinchonidine and their application in the hydrogenation of 1-phenylpropane-1,2-dione and ethyl pyruvate on a supported Pt/Al2O3 catalyst
Busygin, I
Toukoniitty, E
Sillanpää, R
Murzin, DY
Leino, R
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (13) : 2811 - 2821
[10] CARRETERO JC, 2008, SULFONES ASYMMETRIC, pCH9

← 1 2 3 4 5 →