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

[41]

ROSSITER RE, 1985, ASYMMETRIC SYNTHESIS, V5, pCH7

[42] Change in the mode of inhibition of acetylcholinesterase by (4-nitrophenyl)sulfonoxyl derivatives of conformationally constrained choline analogues [J].

Savle, PS ;

Medhekar, RA ;

Kelley, EL ;

May, JG ;

Watkins, SF ;

Fronczek, FR ;

Quinn, DM ;

Gandour, RD .

CHEMICAL RESEARCH IN TOXICOLOGY, 1998, 11 (01) :19-25

[43] PREPARATION OF ALCOHOLS AND 1,2-DIOLS FROM EPOXIDES AND 1,3-DIENES [J].

SELL, MS ;

XIONG, HP ;

RIEKE, RD .

TETRAHEDRON LETTERS, 1993, 34 (38) :6011-6012

[44] A NEW ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLCYSTEINES VIA CHIRAL AZIRIDINES [J].

SHAO, H ;

ZHU, Q ;

GOODMAN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :790-791

[45]

Sharpless K. B., 1993, CATALYTIC ASYMMETRIC, P227

[46]

Steinreiber A, 2000, EUR J ORG CHEM, V2000, P3703

[47]

Steinreiber A, 2001, SYNLETT, P111

[48] SYNTHESES, STRUCTURES, AND ENZYMATIC EVALUATIONS OF CONFORMATIONALLY CONSTRAINED, ANALOG INHIBITORS OF CARNITINE ACETYLTRANSFERASE - (2R,6R)-(CARBOXYLATOMETHYL)-2-(HYDROXYMETHYL)-2,4,4-TRIMETHYLMORPHOLINIUM, (2S,6S)-(CARBOXYLATOMETHYL)-2-(HYDROXYMETHYL)-2,4,4-TRIMETHYLMORPHOLINIUM, (2R,6S)-(CARBOXYLATOMETHYL)-2-(HYDROXYMETHYL)-2,4,4-TRIMETHYLMORPHOLINIUM, AND (2S,6R)-6-(CARBOXYLATOMETHYL)-2-(HYDROXYMETHYL)-2,4,4-TRIMETHYLMORPHOLINIUM [J].

SUN, GB ;

SAVLE, PS ;

GANDOUR, RD ;

ABHAIRD, NN ;

RAMSAY, RR ;

FRONCZEK, FR .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6688-6695

[49] ASYMMETRIC-SYNTHESIS OF (R)-(+)- AND (S)-(-)-2,2,4-TRIMETHYL--4-(HYDROXYMETHYL)-1,3-DIOXOLANE OF HIGH ENANTIOMERIC PURITY [J].

TANNER, D ;

SOMFAI, P .

TETRAHEDRON, 1986, 42 (21) :5985-5990

[50]

Tietze LF, 1998, SYNTHESIS-STUTTGART, P873

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