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

被引：18

作者：

Kim, Ko Hoon ^{[1
,2
]}

Kim, Se Hee ^{[1
,2
]}

Park, Sunhong ^{[3
,4
]}

Kim, Jae Nyoung ^{[1
,2
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea

[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea

[3] Gyeongsang Natl Univ, Dept Chem, Jinju 660701, South Korea

[4] Gyeongsang Natl Univ, Res Inst Nat Sci, Jinju 660701, South Korea

来源：

TETRAHEDRON | 2011年 / 67卷 / 19期

关键词：

Palladium; Heck reaction; Domino reactions; Concerted metalation/deprotonation (CMD); Baylis-Hillman adducts; INTRAMOLECULAR HECK REACTION; C-H ACTIVATION; DIRECT ARYLATION; BIS-CYCLIZATION; ARTOCHAMIN-F; ARYL; FUNCTIONALIZATION; ALKYLATION; CARBON; CONSTRUCTION;

D O I：

10.1016/j.tet.2011.03.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3328 / 3336

页数：9

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