A NEW ALPHA-SELECTIVE SYNTHETIC EQUIVALENT FOR THE CROTYL ANION IN ADDITIONS TO IMINES

被引：19

作者：

BETZ, J ^{[1
]}

HEUSCHMANN, M ^{[1
]}

机构：

[1] UNIV MUNICH,INST ORGAN CHEM,D-80333 MUNICH,GERMANY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 23期

关键词：

D O I：

10.1016/0040-4039(95)00670-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two equivalents of vinylmagnesium bromide add to imines 1 in the presence of cerium trichloride to form homoallylic amines 3 as 2:1-adducts, Z-diastereomers being preferred by a margin of 88:12 to 71:29. Suitable chiral imines 1g-i are transformed to l-products l-3g-i with high diastereoselectivity.

引用

页码：4043 / 4046

页数：4

共 17 条

[1] CHEREST M, 1966, TETRAHEDRON LETT, P875
[2] CRANDALL JK, 1969, TETRAHEDRON LETT, P325
[3] REACTION OF ORGANOLITHIUM REAGENTS WITH ALLYLIC ALCOHOLS
CRANDALL, JK
CLARK, AC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26) : 4236 - 4242
[4] ASYMMETRIC ADDITIONS OF ORGANOLITHIUM REAGENTS TO ALLYLIC ALCOHOLS
DIMMEL, DR
HUANG, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (16) : 2756 - 2760
[5] FELKIN H, 1970, TETRAHEDRON LETT, P4587
[6] ADDITION OF ORGANOLITHIUM REAGENTS TO DOUBLE BOND OF ALLYLIC ALCOHOLS
FELKIN, H
SWIERCZEWSKI, G
TAMBUTE, A
[J]. TETRAHEDRON LETTERS, 1969, (09) : 707 - +
[7] ALLYLCERIUM(III) COMPOUNDS, POWERFUL NEW SYNTHETIC REAGENTS - A NEW STEREOCONTROLLED APPROACH TO OLEFINS AND METHYLENE-INTERRUPTED POLYENES
GUO, BS
DOUBLEDAY, W
COHEN, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4710 - 4711
[8] Hoffmann R. W., 1982, ANGEW CHEM, V94, P569
[9] DIASTEREOGENIC ADDITION OF CROTYLMETAL COMPOUNDS TO ALDEHYDES
HOFFMANN, RW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08): : 555 - 566
[10] REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE
IMAMOTO, T
TAKIYAMA, N
NAKAMURA, K
HATAJIMA, T
KAMIYA, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4392 - 4398

← 1 2 →