STEREOSELECTIVE SYNTHESIS OF 1,3-AMINO ALCOHOLS AND 1,3-AMINO KETONES

被引：46

作者：

BARLUENGA, J ^{[1
]}

AGUILAR, E ^{[1
]}

FUSTERO, S ^{[1
]}

OLANO, B ^{[1
]}

VIADO, AL ^{[1
]}

机构：

[1] UNIV VALENCIA,FAC FARM,DEPT QUIM ORGAN,E-46010 VALENCIA,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 04期

关键词：

D O I：

10.1021/jo00030a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syn,anti-N-Alkyl-1,3-amino alcohols 2 with three chiral centers are synthesized with high stereoselectively by reduction of the corresponding anti-N-acylamino ketones 1 with LiAlH4/TiCl4. The intermediate N-acylamino alcohols 3 can be isolated when DIBALH/ZnCl2 is used instead of the prior reducing system. Cyclic models are proposed to explain the steric course of the reaction in both cases. On the other hand, hydrolysis of tetrahydropyrimidines 8 with 1 N HCl at 25-degrees-C leads to syn-1,3-amino ketones 9 with high stereoselectivity. Several reducing reagents and conditions are tested in the conversion of syn-9 into the subsequent 1,3-amino alcohols. DIBALH/ZnCl2 gives the best results in the last reaction leading to syn,syn-1,3-amino alcohols 10 as practically a single diastereoisomer.

引用

页码：1219 / 1223

页数：5

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