Asymmetric Horner-Wadsworth-Emmons reactions with meso-dialdehydes:: Scope, mechanism, and synthetic applications

被引:0
作者
Rein, T [1 ]
Vares, L
Kawasaki, I
Pedersen, TM
Norrby, PO
Brandt, P
Tanner, D
机构
[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark
[2] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark
[3] Royal Inst Technol, Dept Chem, S-10044 Stockholm, Sweden
关键词
asymmetric Horner-Wadsworth-Emmons reaction; chiral phosphonate; desymmetrization; meso-dialdehyde; chiral heterocycles;
D O I
暂无
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric Homer-Wadsworth-Emmons reactions between chiral phosphonate reagents and various meso-dialdehydes have been investigated. A mechanistic model useful for rationalizing the experimentally observed stereoselectivities is presented. Furthermore; strategies for applying these reactions to the stereocontrolled preparation of chiral heterocyclic building blocks have been developed.
引用
收藏
页码:169 / 172
页数:4
相关论文
共 7 条
[1]   A quantum chemical exploration of the Horner-Wadsworth-Emmons reaction [J].
Brandt, P ;
Norrby, PO ;
Martin, I ;
Rein, T .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1280-1289
[2]   Versatile stereocontrol in kinetic resolution of a diphenylphosphinyl-protected α-amino aldehyde by reaction with chiral phosphonates [J].
Kreuder, R ;
Rein, T ;
Reiser, O .
TETRAHEDRON LETTERS, 1997, 38 (52) :9035-9038
[3]  
NORRBY PO, UNPUB
[4]   THE PICLAVINES, ANTIMICROBIAL INDOLIZIDINES FROM THE TUNICATE CLAVELINA-PICTA [J].
RAUB, MF ;
CARDELLINA, JH ;
SPANDE, TF .
TETRAHEDRON LETTERS, 1992, 33 (17) :2257-2260
[5]   Recent advances in asymmetric Wittig-type reactions [J].
Rein, T ;
Reiser, O .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (04) :369-379
[6]   Zampanolide, a new cytotoxic macrolide from a marine sponge [J].
Tanaka, J ;
Higa, T .
TETRAHEDRON LETTERS, 1996, 37 (31) :5535-5538
[7]  
TULLIS JS, UNPUB