Scope of [1+2+3] annulations using aminonitriles as Michael donors
Scope of [1+2+3] annulations using aminonitriles as Michael donors
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DOI：
10.1021/jo00067a032
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发表时间：
1993-07
影响因子：
3.6
通讯作者：
M. Roux;J. Seyden-penne;L. Wartski;G. Posner;M. Nierlich;D. Vigner;M. Lance
中科院分区：
文献类型：
--
作者：
M. Roux;J. Seyden-penne;L. Wartski;G. Posner;M. Nierlich;D. Vigner;M. Lance
N，N-二甲氨基苯乙腈阴离子（I）作为一个碳原子Michael供体与α，β-不饱和内酯和酮反应，然后烯丙基化中间体烯醇化物，一锅法得到α-单烯丙基化β-取代内酯和环烷酮4a-d，5和6 b。用氰基部分作为离去基团的化合物4a-d和5 b的环化尝试是不成功的。唯一成功的[1+2+3]六环化得到N，N-二甲基氨基反式环稠合双环内酯12 b，用带有烯丙基硅烷部分的6 b进行
The reaction of (N,N-dimethylamino)phenylacetonitrile anion (I) as a one-carbon atom Michael donor toward α,β-unsaturated lactones and ketones followed by allylation of the intermediate enolates provided in a one-pot procedure trans α-monoallylated β-substituted lactones and cyclanones 4a-d, 5, and 6b. Attempts at cyclization of compounds 4a-d and 5b, with the cyano moiety being the leaving group, were unsuccessful. The only successful [1+2+3] hexannulation giving N,N-dimethylamino trans ring-fused bicyclic lactone 12b was run with 6b bearing an allylic silane moiety