Enantiomerically pure gamma-oxidofunctionalised organolithium compounds from chiral oxetanes

被引：24

作者：

Bachki, A

Falvello, LR

Foubelo, F

Yus, M

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,ALICANTE 03080,SPAIN

[2] UNIV ZARAGOZA,FAC CIENCIAS,DEPT QUIM INORGAN,E-50009 ZARAGOZA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(97)00274-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reductive opening of chiral oxetanes 1, ent-1, 4 and 7 with lithium powder and a catalytic amount of DTBB (5 mol%) in THF at 0 degrees C or -20 degrees C, followed by treatment with different electrophiles [H2O, D2O, (BuCHO)-C-t, PhCHO, Me2CO, (CH2)(5)CO and CO2] at -78 degrees C leads, after hydrolysis with water to functionalised alcohols 3, ent-3, 6 and 9. Monoprotected diols 6d and 9d give enantiomerically pure 1,2,5-triols 10 and ent-10 or spirohydroxyethers 11 and ent-11 under acidic conditions in methanol in almost quantitative yield. (C) 1997 Elsevier Science Ltd.

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页码：2633 / 2643

页数：11

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