CATALYTIC ACTIVITY OF CHIRAL BETA-HYDROXYSULFOXIDES IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE

被引：47

作者：

CARRENO, MC

RUANO, JLG

MAESTRO, MC

CABREJAS, LMM

机构：

[1] Departamento de Química (C-I). Facultad

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(00)80181-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first examples of the use of readily available beta-hydroxysulfoxides 1-8 as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde are reported. The increase of the steric hindrance around the chiral ligand OH group improves the e.e. of the obtained 1-phenylpropanol, which is higher with tertiary alcohols (25-45%) than with secondary ones (<23%). The addition of MeAl3 also affords better e.e. (55%).

引用

页码：727 / 734

页数：8

共 26 条

[11] ENANTIOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS - FROM STOICHIOMETRIC TO CATALYTIC ASYMMETRIC INDUCTION
NOYORI, R
SUGA, S
KAWAI, K
OKADA, S
KITAMURA, M
[J]. PURE AND APPLIED CHEMISTRY, 1988, 60 (11) : 1597 - 1606
[12] NOYORI R, 1990, J ORGANOMET CHEM, P382
[13] PICKARD RH, 1914, J CHEM SOC, P1115
[14] ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY SOME CHIRAL LEWIS-ACIDS
REBIERE, F
RIANT, O
KAGAN, HB
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (03) : 199 - 214
[15] ENANTIOSELECTIVE ALKYLATION OF PROCHIRAL ALDEHYDES BY DIETHYLZINC PROMOTED BY (S,S)-1,2-DIPHENYLETHAN-1,2-DIOL
ROSINI, C
FRANZINI, L
PINI, D
SALVADORI, P
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (09) : 587 - 588
[16] RUANO JLG, 1990, AN QUIM, V86, P71
[17] RUANO JLG, 1992, J ORG CHEM, V57, P7235
[18] SHENGJIAN L, 1992, TETRAHEDRON-ASYMMETR, V3, P1467
[19] CHIRAL PIPERAZINE AS A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE ADDITION OF DIALKYL ZINCS TO ARYL ALDEHYDES
SOAI, K
NIWA, S
YAMADA, Y
INOUE, H
[J]. TETRAHEDRON LETTERS, 1987, 28 (41) : 4841 - 4842
[20] CHIRAL N,N-DIALKYLNOREPHEDRINES AS CATALYSTS OF THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALIPHATIC AND AROMATIC-ALDEHYDES - THE ASYMMETRIC-SYNTHESIS OF SECONDARY ALIPHATIC AND AROMATIC ALCOHOLS OF HIGH OPTICAL PURITY
SOAI, K
YOKOYAMA, S
HAYASAKA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) : 4264 - 4268

← 1 2 3 →