ON THE ORIGINS OF STEREOSELECTIVITY IN CHELATION CONTROLLED NUCLEOPHILIC ADDITIONS TO BETA-ALKOXY ALDEHYDES - SOLUTION STRUCTURES OF LEWIS ACID COMPLEXES VIA NMR-SPECTROSCOPY

被引:133
作者
KECK, GE
CASTELLINO, S
机构
关键词
D O I
10.1021/ja00273a060
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:3847 / 3849
页数:3
相关论文
共 13 条
[1]   DIRECT C-13 NUCLEAR MAGNETIC-RESONANCE STUDY OF BORON-TRIFLUORIDE COMPLEXES WITH ALKYL AND CYCLIC KETONES [J].
FRATIELLO, A ;
KUBO, R ;
CHOW, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (11) :1205-1209
[2]   ACYCLIC STEREOSELECTION .22. DIASTEREOFACIAL SELECTIVITY IN THE LEWIS ACID MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL ALDEHYDES AND ENONES [J].
HEATHCOCK, CH ;
KIYOOKA, S ;
BLUMENKOPF, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4214-4223
[3]   CHELATION CONTROLLED DIASTEREOFACIAL SELECTIVITY IN CROTYLTRI-N-BUTYLSTANNANE ADDITIONS TO ALPHA-ALKOXYALDEHYDES [J].
KECK, GE ;
BODEN, EP .
TETRAHEDRON LETTERS, 1984, 25 (18) :1879-1882
[4]   STEREOCHEMICAL CONSEQUENCES FOR THE LEWIS ACID MEDIATED ADDITIONS OF ALLYL AND CROTYLTRI-N-BUTYLSTANNANE TO CHIRAL BETA-HYDROXYALDEHYDE DERIVATIVES [J].
KECK, GE ;
ABBOTT, DE .
TETRAHEDRON LETTERS, 1984, 25 (18) :1883-1886
[5]   OBSERVATIONS ON THE CHOICE OF LEWIS ACID AND MODE OF ADDITION FOR THE LEWIS ACID MEDIATED REACTION OF CROTYLTRI-NORMAL-BUTYLSTANNANE WITH ALDEHYDES - CONVENIENT AND HIGHLY SELECTIVE ACCESS TO BOTH ERYTHRO AND THREO PRODUCTS [J].
KECK, GE ;
ABBOTT, DE ;
BODEN, EP ;
ENHOLM, EJ .
TETRAHEDRON LETTERS, 1984, 25 (36) :3927-3930
[6]  
KECK GE, 1984, TETRAHEDRON LETT, V25, P265, DOI 10.1016/S0040-4039(00)99857-5
[7]   ACYCLIC STEREOSELECTION .20. HIGH DIASTEREOFACIAL SELECTIVITY IN THE STANNIC CHLORIDE MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY ALDEHYDES [J].
KIYOOKA, S ;
HEATHCOCK, CH .
TETRAHEDRON LETTERS, 1983, 24 (44) :4765-4768
[9]   CONCERNING THE MECHANISM OF THE ASYMMETRIC DIELS-ALDER REACTION - 1ST CRYSTAL-STRUCTURE ANALYSIS OF A LEWIS ACID COMPLEX OF A CHIRAL DIENOPHILE [J].
POLL, T ;
METTER, JO ;
HELMCHEN, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :112-114
[10]   1,3-ASYMMETRIC INDUCTION IN ADDITION-REACTIONS OF CHIRAL BETA-ALKOXY ALDEHYDES - EFFICIENT CHELATION CONTROL VIA LEWIS ACIDIC TITANIUM REAGENTS [J].
REETZ, MT ;
JUNG, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) :4833-4835