SYNTHESIS OF EITHER A CIS-FUSED OR TRANS-FUSED HYDROAZULENOL FROM AN ALLYLSTANNANE FUNCTIONALIZED (E)-5-CYCLODECENONE

被引：16

作者：

FAN, WM ^{[1
]}

WHITE, JB ^{[1
]}

机构：

[1] UNIV TEXAS,DEPT CHEM,BOX 19065,ARLINGTON,TX 76019

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 06期

关键词：

TRANSANNULAR CYCLIZATION; ALLYSTANNANE CYCLIZATION; HYDROAZULENE SYNTHESIS; CONTROL OF RELATIVE STEREOCHEMISTRY;

D O I：

10.1016/S0040-4039(00)77464-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)-7-(Tri-n-butylstannyl)-5-cyclodecenone has been synthesized and its transannular cyclization carried out under a variety of conditions. The stereochemistry of the ring fusion in the product hydroazulenol can be controlled through the choice of reaction conditions used to induce cyclization. The use of fluoride anion or sodium naphthalenide led to exclusively the cis ring fusion, while simply heating in benzene led to exclusively the trans ring fusion. Treatment with Lewis and protic acids led to mixtures of the cis- and trans-fused hydroazulenols, which favor the cis isomer.

引用

页码：957 / 960

页数：4

共 13 条

[1] ALLYLSTANNATION .10. STEREOCHEMICAL COURSE OF THE ADDITION-REACTIONS OF (E/Z)-BU3SNCH2CH=CHCH3 WITH ALDEHYDES IN THE PRESENCE OF LEWIS-ACIDS (BU2SNCL2, BF3.ET2O, AND TICL4) [J].