Remote asymmetric induction using chiral sulfoxides

被引:6
作者
Arai, Y [1 ]
机构
[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan
关键词
remote asymmetric induction; chiral sulfoxide; Lewis acid; 1,2-reduction; asymmetric cleavage; 1,4-conjugate addition; Diels-Alder reaction; hetero Diels-Alder reaction; 5-membered aromatic heterocycle;
D O I
10.5059/yukigoseikyokaishi.56.798
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A overview of recent studies on remote asymmetric induction using chiral sulfoxides, with ca. 30 references i.e., a) reductions of sulfinyl ketones, b) C-O bond fission reactions of sulfinyl bicyclic acetals, c) Mukaiyama aldol condensations of sulfinyl aldehydes, and d) hetero Diels-Alder reactions and Diels-Alder reactions of sulfinyl dienophiles, is described. The role of the sulfinyl auxiliary and the Lewis acid, and the stereoselectivities are also analyzed.
引用
收藏
页码:798 / 809
页数:12
相关论文
共 71 条
[1]  
Allin S. M., 1998, ORGANOSULFUR CHEM, V2, P97
[2]   The development and application of 1,3-dithiane 1-oxide derivatives as chiral auxiliaries and asymmetric building blocks for organic synthesis. A review [J].
Allin, SM ;
Page, PCB .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1998, 30 (02) :145-176
[3]  
[Anonymous], SULFUR REPORTS
[4]   ASYMMETRIC INDUCTION IN THE ADDITIONS OF ANIONS OF ALLYLIC SULFOXIDES TO BENZALDEHYDE [J].
ANTONJUK, DJ ;
RIDLEY, DD ;
SMAL, MA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (12) :2635-2651
[5]   DIASTEREOSELECTIVE ADDITION OF ALLYLTRIPHENYL-STANNANE TO 3-SULFINYLFURFURAL MEDIATED BY TITANIUM(IV) TETRACHLORIDE AND TIN(IV) TETRACHLORIDE [J].
ARAI, Y ;
MASUDA, T ;
MASAKI, Y ;
KOIZUMI, T .
HETEROCYCLES, 1994, 38 (08) :1751-1756
[6]  
Arai Y, 1997, SYNLETT, P1459
[7]   A highly asymmetric, Lewis acid-catalysed Diels-Alder reaction using optically active 2-(3-tolyl-p-sulfinyl)furyl alpha,beta-unsaturated ketones as a dienophile [J].
Arai, Y ;
Masuda, T ;
Masaki, Y ;
Shiro, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (08) :759-762
[8]   Highly stereoselective hetero Diels-Alder reactions of chiral 3-(p-tolylsulfinyl)-2-furaldehyde with Danishefsky's diene promoted by a lanthanoid Lewis acid [J].
Arai, Y ;
Masuda, T ;
Masaki, Y ;
Shiro, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1199-1204
[9]   DIASTEREOSELECTIVE ALLYLATION OF CHIRAL SULFINYL-SUBSTITUTED THIOPHENECARBALDEHYDES WITH A LEWIS-ACID [J].
ARAI, Y ;
SUZUKI, A ;
MASUDA, T ;
MASAKI, Y ;
SHIRO, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (22) :2913-2917
[10]   Recoverable chiral sulfoxide: Asymmetric Diels-Alder reaction using optically active 1-(2-p-tolysulfinyl)pyrrolyl alpha,beta-unsaturated ketones as a dienophile [J].
Arai, Y ;
Masuda, T ;
Masaki, Y .
CHEMISTRY LETTERS, 1997, (02) :145-146