Stereoselective synthesis of 1,2-amino alcohols by addition of organocuprate center-dot BF3 complexes and organolithium reagents to an alpha-silyloxyaldimine derived from (S)-ethyl lactate

被引：32

作者：

Ishimaru, K ^{[1
]}

Tsuru, K ^{[1
]}

Yabuta, K ^{[1
]}

Wada, M ^{[1
]}

Yamamoto, Y ^{[1
]}

Akiba, K ^{[1
]}

机构：

[1] HIROSHIMA UNIV, FAC SCI, DEPT CHEM, HIGASHIHIROSHIMA 739, JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 41期

关键词：

D O I：

10.1016/0040-4020(96)00776-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Amino alcohols were synthesized by addition of organocuprate . BF3 2 (R=n-Bu, n-octyl, Me, phenethyl, Ph), organocopper . BF3 3 (R=Me, n-Bu), and organolithiums (R=n-Bu, n-octyl, Me, phenethyl, Ph) to an alpha-silyloxyaldimine 1 derived from commercially available (S)-ethyl lactate. The reactions with organocuprate . BF3 2 and organocopper . BF3 3 led to the anti isomers almost exclusively (anti:syn=>98:<2 for R=n-Bu, n-octyl, Me, phenethyl and anti:syn=95:5 for R=Ph, 52-93% isolated yields) and the syn isomers could be obtained with high stereoselectivities by using organolithiums (anti:syn=10:90-20:80, 41-71% isolated yields). Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：13137 / 13144

页数：8

共 28 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

Anh N.T., 1980, TOP CURR CHEM, V88, P145

[3] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].

BLASER, HU .

CHEMICAL REVIEWS, 1992, 92 (05) :935-952

[4] DIASTEREOSELECTIVE ALLYLATION OF CHIRAL IMINES - NOVEL APPLICATION OF ALLYLCOPPER REAGENTS TO THE ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYL AMINES [J].

BOCOUM, A ;

BOGA, C ;

SAVOIA, D ;

UMANIRONCHI, A .

TETRAHEDRON LETTERS, 1991, 32 (10) :1367-1370

[5] SYNTHESIS OF (S)-2-AMINO-1,1-DIPHENYLBUTAN-4-OL - CONVERSION OF AN ALPHA-AMINO-ACID INTO AN ALPHA-(DIPHENYLMETHYL) AMINE WITHOUT LOSS OF OPTICAL PURITY [J].

BOYLE, PH ;

DAVIS, AP ;

DEMPSEY, KJ ;

HOSKEN, GD .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2819-2828

[6] REVERSAL OF DIASTEREOSELECTIVITY IN THE ADDITION OF C-NUCLEOPHILES TO N-TRIMETHYLSILYL IMINES VIA GRIGNARD DERIVED ORGANO COPPER-BORON TRIFLUORIDE REAGENTS [J].

CAINELLI, G ;

GIACOMINI, D ;

PANUNZIO, M ;

ZARANTONELLO, P .

TETRAHEDRON LETTERS, 1992, 33 (50) :7783-7786

[7]

CHEREST M, 1968, TETRAHEDRON LETT, V18, P2199

[8] STEREOSELECTIVE SYNTHESIS OF (3R,4S)-STATINE UTILIZING THE IRON ACETYL COMPLEX [(ETA-5-C5H5)FE(CO)(PPH3)COME] AS A CHIRAL ACETATE ENOLATE EQUIVALENT [J].

COOKE, JWB ;

DAVIES, SG ;

NAYLOR, A .

TETRAHEDRON, 1993, 49 (36) :7955-7966

[9] ANISOTROPIC EXTINCTION CORRECTION IN ZACHARIASEN APPROXIMATION [J].

COPPENS, P ;

HAMILTON, WC .

ACTA CRYSTALLOGRAPHICA SECTION A-CRYSTAL PHYSICS DIFFRACTION THEORETICAL AND GENERAL CRYSTALLOGRAPHY, 1970, A 26 :71-&

[10] SYNTHESIS AND INVESTIGATION OF A HINDERED, CHIRAL, BICYCLIC GUANIDINE [J].

DAVIS, AP ;

DEMPSEY, KJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2829-2840

← 1 2 3 →