HIGHLY ENANTIOSELECTIVE ALKYLATION OF CARBON-NITROGEN DOUBLE-BONDS - CATALYTIC AND STOICHIOMETRIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE AMINES BY THE ENANTIOSELECTIVE ADDITION OF DIALKYLZINC REAGENTS TO N-DIPHENYLPHOSPHINOYLIMINES

被引：128

作者：

SOAI, K

HATANAKA, T

MIYAZAWA, T

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 16期

关键词：

D O I：

10.1039/c39920001097

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first highly enantioselective alkylation of carbon-nitrogen double bonds (of N-diphenylphosphinoylimines) with dialkylzinc reagents promoted by chiral amino alcohols afforded optically active phosphoramides (precursors of amines) in up to 91% enantiomeric excess.

引用

页码：1097 / 1098

页数：2

共 14 条

[1] ASYMMETRIC REDUCTION OF PHOSPHINYL IMINES WITH HYDRIDE REAGENTS - ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PRIMARY AMINES
HUTCHINS, RO
ABDELMAGID, A
STERCHO, YP
WAMBSGANS, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) : 702 - 704
[2] ENANTIOSELECTIVE ALKYLATION OF N-(TRIMETHYLSILYL)BENZALDEHYDE IMINE
ITSUNO, S
YANAKA, H
HACHISUKA, C
ITO, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05): : 1341 - 1342
[3] THE TITANIUM TETRACHLORIDE INDUCED SYNTHESIS OF N-PHOSPHINOYLIMINES AND N-SULPHONYLIMINES DIRECTLY FROM AROMATIC-ALDEHYDES
JENNINGS, WB
LOVELY, CJ
[J]. TETRAHEDRON, 1991, 47 (29) : 5561 - 5568
[4] ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION
NOYORI, R
KITAMURA, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) : 49 - 69
[5] PHOSPHINAMIDES - A NEW CLASS OF AMINO PROTECTING GROUPS IN PEPTIDE-SYNTHESIS
RAMAGE, R
HOPTON, D
PARROTT, MJ
KENNER, GW
MOORE, GA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (06): : 1357 - 1370
[6] COMPLEMENTARY CATALYTIC ASYMMETRIC INDUCTION IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
SOAI, K
OOKAWA, A
OGAWA, K
KABA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (06) : 467 - 468
[7] A NEW CHIRAL CATALYST FOR THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINC REAGENTS TO ALIPHATIC-ALDEHYDES
SOAI, K
YOKOYAMA, S
EBIHARA, K
HAYASAKA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) : 1690 - 1691
[8] ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO ENONES USING CHIRAL BETA-AMINOALCOHOL AS CHIRAL CATALYST OR LIGAND
SOAI, K
OKUDO, M
OKAMOTO, M
[J]. TETRAHEDRON LETTERS, 1991, 32 (01) : 95 - 96
[9] 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
[10] CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES USING CHIRAL PYRROLIDINYLMETHANOLS AND THEIR METAL-SALTS
SOAI, K
OOKAWA, A
KABA, T
OGAWA, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) : 7111 - 7115

← 1 2 →