LIGAND ASSISTED ASYMMETRIC-SYNTHESIS .2. DIASTEREOSELECTIVE DIELS-ALDER ADDITIONS WITH LEWIS ACID ATTRACTING AUXILIARIES DERIVED FROM PENTITOLS

被引:13
作者
GRAS, JL [1 ]
PONCET, A [1 ]
NOUGUIER, R [1 ]
机构
[1] FAC SCI & TECH ST JEROME,CHIM ORGAN LAB B,CNRS,F-13397 MARSEILLE 13,FRANCE
关键词
ASYMMETRIC DIELS-ALDER REACTION; ALDITOL; PENTITOL; METHYLENE ACETAL;
D O I
10.1016/S0040-4039(00)92078-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dimethylene acetals of the three pentitols and methylene acetal of 1,2,4-butanetriol behave as effective templates for the diastereoselective Diels-Alder reaction. The chirality transfer occurs through a chelate-complex involving one of the dioxane rings.
引用
收藏
页码:3323 / 3326
页数:4
相关论文
共 26 条
[1]   CARBOHYDRATE CYCLIC ACETAL FORMATION AND MIGRATION [J].
CLODE, DM .
CHEMICAL REVIEWS, 1979, 79 (06) :491-513
[2]   CHELATION AND NON-CHELATION DIRECTED CLEAVAGE OF ACETALS [J].
CORCORAN, RC .
TETRAHEDRON LETTERS, 1990, 31 (15) :2101-2104
[3]   THE ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE AND DIOXOLANE ACETALS - SOLUTION STRUCTURE OF THEIR LEWIS ACID COMPLEXES [J].
DENMARK, SE ;
WILLSON, TM ;
ALMSTEAD, NG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9258-9260
[4]  
FELDER H, 1986, HELV CHIM ACTA, V69, P1137
[5]   ASYMMETRIC-SYNTHESIS WITH LIGANDS .1. MODELS OF CHIRAL AUXILIARIES FOR ENANTIOSELECTIVE DIELS-ALDER REACTION [J].
GRAS, JL ;
PELLISSIER, H .
TETRAHEDRON LETTERS, 1991, 32 (48) :7043-7046
[6]   TRANSACETALATION OF TRIOLS FROM DIMETHOXYMETHANE - SELECTIVITY AND SYNTHETIC APPLICATIONS [J].
GRAS, JL ;
NOUGUIER, R ;
MCHICH, M .
TETRAHEDRON LETTERS, 1987, 28 (52) :6601-6604
[7]  
GRAS JL, 1992, SYNTHETIC COMMUN, V22, P405
[8]   STEREOSELECTIVE OPENING OF ACETALS DERIVED FROM DIMETHYL TARTRATE [J].
GUINDON, Y ;
SIMONEAU, B ;
YOAKIM, C ;
GORYS, V ;
LEMIEUX, R ;
OGILVIE, W .
TETRAHEDRON LETTERS, 1991, 32 (40) :5453-5456
[9]   (D),(L)-1,3 2,4-Dimethylene-adonitol and 2,4-methylene-adonitol [J].
Hann, RM ;
Hudson, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1906-1908
[10]   2,4 3,5-dimethylene-D,L-xyhtol and 2,4-methylene-xylitol [J].
Hann, RM ;
Ness, AT ;
Hudson, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :670-673