New 2-acyl-1,3-dioxane derivatives from (1R)-(-)-myrtenal:: stereochemical effect on their relative ability as chiral auxiliaries

被引：15

作者：

Becerra-Martinez, Elvia ^{[1
]}

Velazquez-Poncea, Pedro ^{[1
]}

Sanchez-Aguilar, Miguel A. ^{[1
]}

Rodriguez-Hosteguin, Alfredo ^{[1
]}

Joseph-Nathan, Pedro ^{[2
]}

Taniariz, Joaquin ^{[1
]}

Zepeda, L. Gerardo ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Mexico City 11340, DF, Mexico

[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 23期

关键词：

D O I：

10.1016/j.tetasy.2007.10.047

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Four 3,10-pinanediol derivatives 1a-d, prepared in 50-72% global yields from (IR)-(-)-myrtenal 2, were treated with (RO)(2)CHCOR3 (R-3 = CH3, Ph) to afford 2-acyl-1,3-dioxanes 3a-f. The latter were submitted to nucleophilic additions using several Grignard reagents to mainly afford carbinols generated by re diastereofacial attack (85-99% yield, >= 88:12 dr). The lowest diastereoselectivity was observed when PhLi or hydrides were used as nucleophiles. Only an equatorial substituent at C-3 modifies the diastereoselectivity of the nucleophilic additions. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2727 / 2737

页数：11

共 15 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].