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.
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收藏
页码：2933 / 2936
页数：4
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