N-BOC 2-ACYLOXAZOLIDINES - USEFUL PRECURSORS TO ENANTIOPURE 1,2-DIOLS VIA HIGHLY DIASTEREOSELECTIVE NUCLEOPHILIC ADDITIONS

被引：45

作者：

AGAMI, C

COUTY, F

LEQUESNE, C

机构：

[1] Laboratoire de Synthèse Asymétrique (URA CNRS 408), Université Pierre et Marie Curie, 75005 Paris

来源：

TETRAHEDRON | 1995年 / 51卷 / 14期

关键词：

D O I：

10.1016/0040-4020(95)00145-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Boc 2-Acyloxazolidines were synthesized from norephedrine and phenylglycinol. This preparation involves: (i) a transformation of the above beta-amino alcohols into N-Boc 2-ethoxycarbonyloxazolidines, (ii) the formation of the corresponding Weinreb amides and, (iii) a reaction between these amides and organometallic reagents. Such diastereomerically pure heterocycles react cleanly with various nucleophilic reagents (Grignard reagents, sodium borohydride and allylsilane) to afford the corresponding alcohols. Treatment of these hydroxyoxazolidines with trifluoro acetic acid, followed by hydrolysis and reduction of the intermediate alpha-hydroxy aldehydes afforded 1,2-diols. The overall transformation exhibited in most cases a complete diastereoselectivity which can be explained by a chelated model for the nucleophilic addition.

引用

页码：4043 / 4056

页数：14

共 30 条

[1] Eliel, Asymmetric Synthesis, 2, pp. 125-155, (1983)
[2] Mukaiyama, Sakito, Asami, ASYMMETRIC SYNTHESIS OF α-HYDROXY ALDEHYDES, Chemistry Letters, pp. 1253-1256, (1978)
[3] Ukaji, Yamamoto, Fukui, Fujisawa, Tetrahedron Lett., 32, pp. 2919-2922, (1991)
[4] Thiam, Chastrette, Tetrahedron Lett., 31, pp. 1429-1432, (1990)
[5] Heitz, Gellibert, Mioskowski, Tetrahedron Lett., 27, pp. 3859-3860, (1986)
[6] Alexakis, Lensen, Tranchier, Mangeney, J. Org. Chem., 57, pp. 4563-4565, (1992)
[7] Agami, Rizk, Tetrahedron, 41, pp. 537-540, (1985)
[8] Arsenyadis, Huang, Morellet, Beloeil, Husson, Heterocycles, 31, pp. 1789-1799, (1990)
[9] Bernardi, Cardani, Scolastico, Villa, Tetrahedron, 46, pp. 1987-1998, (1990)
[10] Pasquarello, Poli, Scolastico, Stereoselective Reduction of 2-Methylacetoacetaldehydes Protected as Norephedrine-Derived Oxazolidines: A New Access to Enantiomerically Pure "Propanal-Type" Aldols, Synlett, pp. 93-95, (1992)

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