Metal dependent 1,3-asymmetric induction in the retro-[1,4]-Brook rearrangement of a silylated tiglyl alkalimetal compound

被引：9

作者：

Gibson, C

Buck, T

Noltemeyer, M

Bruckner, R

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY

[2] UNIV GOTTINGEN,INST ANORGAN CHEM,D-37077 GOTTINGEN,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(97)00516-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

At -78 degrees C in THF, the tiglyl phenyl sulfide 5 and lithium naphthalenide gave a tiglyl lithium species which underwent an irreversible retro-[1,4]-Brook rearrangement giving rise to a 22:78 mixture of the anti,trans and the syn,trans diastereomer of the tiglyl silane 6. The same sulfide 5 and potassium naphthalenide provided the same products anti,trans- and syn,trans-6 as a 96:4 mixture. This time they arose from the reversible retro-[1,4]-Brook rearrangement of a tiglyl potassium intermediate. (C) 1997 Elsevier Science Ltd.

引用

页码：2933 / 2936

页数：4

共 19 条

[1]

[Anonymous], 1994, ANGEW CHEM, V106, P220

[2]

BEHRENS K, 1995, LIEBIGS ANN, P385

[3]

Brook A. G., 1980, REARRANGEMENTS GROUN, P149

[4] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].