Palladium-Catalyzed α-Arylation of Meyers's Chiral Bicyclic Lactams and a Deprotonative Ring-Opening Sideline

被引：1

作者：

Chiang, Hsin-Lun ^{[1
]}

Zhao, Wei-Ting ^{[1
]}

Chen, Yi-An ^{[1
]}

Lin, Yi-Ching ^{[1
]}

Chen, Pei-Lin ^{[2
]}

Wu, Yen-Ku ^{[1
]}

机构：

[1] Natl Yang Ming Chiao Tung Univ, Dept Appl Chem, 1001 Univ Rd, Hsinchu 30010, Taiwan

[2] Natl Tsing Hua Univ, Instrumentat Ctr, 101,Sect 2,Kuang Fu Rd, Hsinchu 30013, Taiwan

来源：

SYNLETT | 2024年 / 35卷 / 10期

关键词：

arylation; palladium catalysis; enolates; rearrangement; stereoselectivity; lactams; ASYMMETRIC-SYNTHESIS; ROUTE;

D O I：

10.1055/a-2258-3788

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described is a deprotonative alpha-arylation reaction of Mey-ers's chiral bicyclic lactams (MCBLs) under palladium catalysis, and asubstrate-dependent post-transformation. When the bridgehead car-bon of the MCBLs is substituted with a methyl or an ethyl group, theinitial arylation product undergoes a further rearrangement reaction togive a conjugated framework. On the other hand, substrates bearing abridgehead isopropyl or aryl group are converted into the correspond-ing exo-arylation products. Preliminary studies indicated that the rear-rangement pathway was promoted by deprotonation and was indepen-dent of palladium catalysis. In addition to mechanistic interests, thisstudy demonstrates a modular and divergent synthesis of functional-ized lactams

引用

页码：1145 / 1148

页数：4

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