Synthesis of (-)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin

被引：3

作者：

Bravo, P

Corradi, E

Frigerio, M

Meille, SV

Panzeri, W

Pesenti, C

Viani, F

机构：

[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy

[2] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 34期

关键词：

sulfoxides; epoxides; diastereoselection; trifluorofrontalin;

D O I：

10.1016/S0040-4039(99)01186-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of enantiomerically pure (-)-(1S,5R)-1-trifluoromethyl frontalin 7 starting from (-)-(1R)-menthyl (S)-toluene-4-sulfinate, 5-pentenylmagnesium bromide and methyl trifluoroacetate is described. The synthetic procedures to obtain the enantiomer (+)-(1R,5S)-7 are also mentioned. Absolute stereochemistry was unambiguously assigned by X-ray analysis of intermediates 3 and 5. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6317 / 6320

页数：4

共 11 条

[1] Highly diastereoselective methylene transfer from diazomethane to the carbonyl of β-keto sulfoxides.: A general approach to synthetically versatile fluorine-containing chiral building blocks. [J].