Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol

被引：42

作者：

Curti, Claudio ^{[1
]}

Ranieri, Beatrice ^{[1
]}

Battistini, Lucia ^{[1
]}

Rassu, Gloria ^{[2
]}

Zambrano, Vincenzo ^{[2
]}

Pelosi, Giorgio ^{[3
]}

Casiraghi, Giovanni ^{[1
]}

Zanardi, Franca ^{[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 Chim Analit Chim Fi, I-43124 Parma, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 11-12期

关键词：

asymmetric catalysis; asymmetric synthesis; diastereoselectivity; enantioselectivity; heterocyclic dienoxy silanes; vinylogous aldol reaction; ENANTIOSELECTIVE TOTAL-SYNTHESIS; C(2)-SYMMETRIC COPPER(II) COMPLEXES; SILYL KETENE ACETALS; CHIRAL LEWIS-ACIDS; ABSOLUTE-CONFIGURATION; CHIROPTICAL PROPERTIES; ADDITION-REACTIONS; VARIABLE STRATEGY; ACTIVATION; 2-TRIMETHYLSILYLOXYFURAN;

D O I：

10.1002/adsc.201000189

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Denmark's chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vmylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of delta-hydroxylated gamma-butenolide-type frameworks with high efficiency and valuable margins of regio-. diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol. with syn-configured aldol adducts emerging from pyrroles bearing electron-withdrawing N-protecting groups (Boc, Ts. and Cbz) and anti-con figured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.

引用

页码：2011 / 2022

页数：12

共 80 条

[1] Silicon tetrachloride in organic synthesis: new applications for the vinylogous aldol reaction [J].