Synthesis of enantiopure syn-beta-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to alpha-(dibenzylamino) aldehydes

被引：64

作者：

Andres, JM ^{[1
]}

Barrio, R ^{[1
]}

Martinez, MA ^{[1
]}

Pedrosa, R ^{[1
]}

PerezEncabo, A ^{[1
]}

机构：

[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 13期

关键词：

D O I：

10.1021/jo960017t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral alpha-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.

引用

页码：4210 / 4213

页数：4

共 29 条

[1] ENANTIOSELECTIVE ETHYLATION OF ALDEHYDES CATALYZED BY CHIRAL C-2-SYMMETRICAL BETA-HYDROXY-M-XYLYLENE DIAMINES
ANDRES, JM
MARTINEZ, MA
PEDROSA, R
PEREZENCABO, A
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (01) : 67 - 72
[2] BOERSMA J, 1982, COMPREHENSIVE ORGANO, pCH16
[3] CRCL2 MEDIATED ALLYLATION OF N-PROTECTED ALPHA-AMINO ALDEHYDES - A VERSATILE SYNTHESIS OF POLYPEPTIDES CONTAINING AN HYDROXYETHYLENE ISOSTERE
CIAPETTI, P
TADDEI, M
ULIVI, P
[J]. TETRAHEDRON LETTERS, 1994, 35 (19) : 3183 - 3186
[4] COREY EJ, 1976, TETRAHEDRON LETT, V11, P809
[5] DONDONI A, 1995, SYNTHESIS-STUTTGART, P181
[6] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES
DONDONI, A
FANTIN, G
FOGAGNOLO, M
PEDRINI, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1439 - 1446
[7] GOLEBIOWSKI A, 1993, SYNLETT, P241
[8] HENEGHAN M, 1992, SYNLETT, P489
[9] TITANATED METHOXYALLENE AS NOVEL HOMOALDOL EQUIVALENT FOR DIASTEREOSELECTIVE ADDITIONS TO CHIRAL AMINO ALDEHYDES
HORMUTH, S
REISSIG, HU
DORSCH, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (10): : 1449 - 1450
[10] HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-(2R,3S)-3-HYDROXYPROLINE
JURCZAK, J
PROKOPOWICZ, P
GOLEBIOWSKI, A
[J]. TETRAHEDRON LETTERS, 1993, 34 (44) : 7107 - 7110

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