Palladium-catalyzed synthesis of indane and cyclobuta[<em>a</em>]indenes from homoallylic alcohols derived from Baylis-Hillman adducts: base-dependent stereoselectivity for the benzylidene group in cyclobuta[<em>a</em>]indene期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Palladium-catalyzed synthesis of indane and cyclobuta[a]indenes from homoallylic alcohols derived from Baylis-Hillman adducts: base-dependent stereoselectivity for the benzylidene group in cyclobuta[a]indene

Authors:	Ko Hoon KimSe Hee Kim Sunhong ParkJae Nyoung Kim

Affiliation:	^a Department of Chemistry and Institute of Basic Science, Chonnam National University, Gwangju 500-757, Republic of Korea ^b Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University, Jinju 660-701, Republic of Korea

Abstract:	Various indane and cyclobuta[a]indene derivatives were synthesized by palladium-catalyzed cyclization of homoallylic alcohol derivatives prepared from Baylis-Hillman adducts. Especially, cyclobuta[a]indene derivative was synthesized stereoselectively by palladium-catalyzed 5-exo-trig/4-exo-trig cascade cyclization, albeit in moderate yield. The Z isomer was formed exclusively in the presence of Et₃N by usual Heck-type carbopalladation process while E isomer with Cs₂CO₃ most likely by a concerted metalation/deprotonation (CMD) process.

Keywords:	Palladium Heck reaction Domino reactions Concerted metalation/deprotonation (CMD) Baylis-Hillman adducts
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