Dramatic Base-Oriented Chemoselective Tandem Wacker Cyclizations: Synthesis of Bisbenzannelated Spiroketals and 2-Substituted Chromans

被引：13

作者：

Xin, Zhijun ^{[1
]}

Zhang, Yuan ^{[1
]}

Tao, Hua ^{[1
]}

Xue, Jijun ^{[1
]}

Li, Ying ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

SYNLETT | 2011年 / 11期

基金：

中国国家自然科学基金;

关键词：

palladium; chemoselectivity; spiroketals; chromans; Wacker cyclization; PALLADIUM-CATALYZED CYCLIZATION; GAMMA-RUBROMYCIN; STEREOSELECTIVE-SYNTHESIS; AEROBIC DIALKOXYLATION; CONVERGENT ROUTE; HUMAN TELOMERASE; DNA HELICASE; PURPUROMYCIN; SKELETON; CORE;

D O I：

10.1055/s-0030-1260775

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(II)/Cu(II)-catalyzed chemoselective tandem aerobic cyclization of phenolic olefins leads to [5,6]-bisbenzannelated spiroketals or 2-substituted chromans, wherein it was interestingly found that the presence or absence of base could be responsible for the tunable selectivity. The [5,6]-bisbenzannelated spiroketals were achieved from tandem Wacker cyclization-aroxylation in moderate yields in the absence of base, and 2-substituted chromans were formed through base-mediated Pd(II)/Cu(II)-catalyzed tandem Wacker cyclization-Michael addition in good yields.

引用

页码：1579 / 1584

页数：6

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