ENANTIOSELECTIVE PREPARATION OF C-2-SYMMETRICAL 1,4-DIOLS

被引：31

作者：

VETTEL, S ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(00)78200-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective addition of functionalized dialkylzincs to the gamma-alkoxyaldehydes 5, 6 and 7 provides 1,4-diols 1-3 with 73-99 %ee. After a simple reaction sequence, these diols are converted to chiral gamma-alkoxyaldehydes which undergo a second catalytic enantioselective addition of the same diorganozinc providing C-2-symmetrical 1,4-diols 10a-f with excellent diastereoselectivity (up to 97:3)

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页码：5849 / 5852

页数：4

相关论文

共 23 条

[1] NEW CHIRAL PHOSPHOLANES - SYNTHESIS, CHARACTERIZATION, AND USE IN ASYMMETRIC HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

HARLOW, RL .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :569-592

[2] C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519

[3]

KIM MJ, 1993, SYNLETT, P767

[4] A NEW CATALYTIC ASYMMETRIC APPROACH TO POLYFUNCTIONAL ALDOL PRODUCTS MEDIATED BY ZINC ORGANOMETALLICS [J].

KNOCHEL, P ;

BRIEDEN, W ;

ROZEMA, MJ ;

EISENBERG, C .

TETRAHEDRON LETTERS, 1993, 34 (37) :5881-5884

[5] A SIMPLE SYNTHESIS OF (S,S)-2,5-HEXANEDIOL [J].

LIESER, JK .

SYNTHETIC COMMUNICATIONS, 1983, 13 (09) :765-767

[6] A LEVOGLUCOSENONE-DERIVED SYMMETRICAL CHIRON [J].

MORIN, C .

TETRAHEDRON LETTERS, 1993, 34 (32) :5095-5096

[7]

NOWOTNY S, 1994, IN PRESS TETRAHEDRON, V35

[8] H-1 AND H-2 NUCLEAR MAGNETIC-RESONANCE DETERMINATION OF THE ENANTIOMERIC PURITY AND ABSOLUTE-CONFIGURATION OF ALPHA-DEUTERIATED PRIMARY CARBOXYLIC-ACIDS, ALCOHOLS, AND AMINES [J].

PARKER, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (01) :83-88

[9] ENANTIOSELECTIVE SYNTHESIS OF THE TOP HALF OF TETRONOLIDE [J].

ROUSH, WR ;

KOYAMA, K .

TETRAHEDRON LETTERS, 1992, 33 (42) :6227-6230

[10] PREPARATION OF FUNCTIONALIZED DIALKYLZINC REAGENTS VIA AN IODINE ZINC EXCHANGE-REACTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF FUNCTIONALIZED SECONDARY ALCOHOLS [J].

ROZEMA, MJ ;

SIDDURI, A ;

KNOCHEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1956-1958