Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2-oxazolidinones: asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377

被引：7

作者：

Sugiyama, Shigeo ^{[1
]}

Arai, Satoshi ^{[1
]}

Ishii, Keitaro ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Dept Life & Pharmaceut Sci, Tokyo 2048588, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 38期

关键词：

Asymmetric desymmetrization; Serinol; Oxazolidinone; Debenzylation; Fractional crystallization; Cyclic carbonate; TRANSFER-CATALYTIC ALKYLATION; AMINO-ACID DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SELF-REGENERATION; ALPHA; ALPHA-DIALKYL-ALPHA-AMINO ACIDS; IMMUNOMODULATOR (+)-CONAGENIN; ENANTIOSPECIFIC SYNTHESIS; CONVENIENT PREPARATION; RECENT PROGRESS;

D O I：

10.1016/j.tet.2012.06.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reaction of (S)-2-benzyl-2-(alpha-methylbenzyl)amino-1,3-propanediol (S)-4a and 2-chloroethyl chloroformate, and the subsequent addition of DBU gave (4R,alpha S)-4-benzyl-4-hydroxymethyl-3-(alpha-methylbenzyl)-2-oxazolidinone (4R)-5a (92% de) via a diastereoselective asymmetric desymmetrization process. Debenzylation of (4R)-5a using trifluoromethanesulfonic acid and anisole in MeNO2 gave (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone (R)-15a, which was converted into (R)-(alpha-hydroxymethyl) phenylalanine (7) in two steps. N-Boc-alpha-methylphenylalanine (8), cericlamiOne (9) and BIRT-377 (10) were also synthesized using these asymmetric desymmetrization and debenzylation. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：8033 / 8045

页数：13