An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

被引：26

作者：

Avenoza, A ^{[1
]}

Cativiela, C

Peregrina, JM

Sucunza, D

Zurbano, MM

机构：

[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim La Rioja, UA CSIC, Logrono 26006, Spain

[2] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(01)00230-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1383 / 1388

页数：6

共 57 条

[11]

FINN MG, 1985, ASYMMETRIC SYNTHESIS, V5, pCH8

[12] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[13] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[14] The diastereoselective epoxidation of olefins in supercritical carbon dioxide. [J].

Haas, GR ;

Kolis, JW .

TETRAHEDRON LETTERS, 1998, 39 (33) :5923-5926

[15] ANOMALOUS ENANTIOSELECTIVITY IN THE SHARPLESS CATALYTIC ASYMMETRIC DIHYDROXYLATION REACTION OF 1,1-DISUBSTITUTED ALLYL ALCOHOL DERIVATIVES [J].

HALE, KJ ;

MANAVIAZAR, S ;

PEAK, SA .

TETRAHEDRON LETTERS, 1994, 35 (03) :425-428

[16] THE SYNTHETIC METHODOLOGY OF NONRACEMIC GLYCIDOL AND RELATED 2,3-EPOXY ALCOHOLS [J].

HANSON, RM .

CHEMICAL REVIEWS, 1991, 91 (04) :437-475

[17] PROCEDURE FOR THE CATALYTIC ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS IN THE PRESENCE OF MOLECULAR-SIEVES [J].

HANSON, RM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1922-1925

[18] Total synthesis of (+)-conagenin [J].

Hatakeyama, S ;

Fukuyama, H ;

Mukugi, Y ;

Irie, H .

TETRAHEDRON LETTERS, 1996, 37 (23) :4047-4050

[19] Et(2)AlCl-catalyzed cyclization of epoxytrichloroacetimidates for the synthesis of alpha-substituted serines [J].

Hatakeyama, S ;

Matsumoto, H ;

Fukuyama, H ;

Mukugi, Y ;

Irie, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2275-2279

[20] SYNTHESIS OF NATURAL AND UNNATURAL FRONTALIN [J].

HOSOKAWA, T ;

MAKABE, Y ;

SHINOHARA, T ;

MURAHASHI, SI .

CHEMISTRY LETTERS, 1985, (10) :1529-1530

← 1 2 3 4 5 6 →