Synthesis and highly diastereoselective alkylation of chiral N-[(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines

被引：7

作者：

Katritzky, AR ^{[1
]}

ElZemity, SR ^{[1
]}

Leeming, P ^{[1
]}

Hartshorn, CM ^{[1
]}

Steel, PJ ^{[1
]}

机构：

[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 06期

关键词：

chiral triazole; C-2-symmetry; diastereoselectivity; Grignard reagents; hydrazones;

D O I：

10.1016/0957-4166(96)00196-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(S,S)-4-Amino-35-bis(1-hydroxyethyl)-1,2,4-triazole 2 (SAT) (from (S)-lactic acid and hydrazine hydrate) reacted with substituted benzaldehydes 6 to afford N-[(S,S)-3,5-bis(1-hydroxyethyl)-1,2,4-triazol-4-yl]arylimines 3 in excellent yield. Protection of the hydroxyl groups in compounds 3 was accomplished using methyl tosylate under mild conditions to give N-[(S, S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines 4 in very high yield. Subsequent reactions of 4 with Grignard reagents afforded compounds 5 with good to excellent diastereoselectivities in good yield. (C) 1986 Elsevier Science Ltd

引用

页码：1621 / 1630

页数：10