Catalytic, Asymmetric Hypervinylogous Mukaiyama Aldol Reactions of Extended Furan-Based Silyl Enolates

被引：24

作者：

Curti, Claudio ^{[1
]}

Battistini, Lucia ^{[1
]}

Sartori, Andrea ^{[1
]}

Lodola, Alessio ^{[1
]}

Mor, Marco ^{[1
]}

Rassu, Gloria ^{[2
]}

Pelosi, Giorgio ^{[3
]}

Zanardi, Franca ^{[1
]}

Casiraghi, Giovanni ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Farmaceut, I-43124 Parma, Italy

[2] CNR, Ist Chim Biomol, I-07100 Sassari, Italy

[3] Univ Parma, Dipartimento Chim Gen & Inorgan, I-43124 Parma, Italy

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 17期

关键词：

VINYLOGOUS ALDOL; ADDITION-REACTIONS; PRINCIPLE;

D O I：

10.1021/ol2020626

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Virtually perfect transmittal of the enolate reactivity up to five conjugated double bonds from the origin allows a series of furan-based silyloxypolyenes to add to aldehyde carbonyls at the most distant point of the molecule. Denmark's axially chiral bisphosphoramide/SlCl(4) combination catalyzes these scantly precedented, long-range Mukaiyama-type vinylogous aldol reactions efficiently, providing a palette of extended gamma-alkylidene butenolide carbinois with complete omega-site selectivity and good to excellent levels of enantioselectivity.

引用

收藏

页码：4738 / 4741

页数：4

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