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Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole‐ and Furan‐Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol
Author(s) -
Curti Claudio,
Ranieri Beatrice,
Battistini Lucia,
Rassu Gloria,
Zambrano Vincenzo,
Pelosi Giorgio,
Casiraghi Giovanni,
Zanardi Franca
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000189
Subject(s) - chemistry , aldol reaction , lewis acids and bases , furan , heteroatom , silanes , organic chemistry , pyrrole , lewis acid catalysis , adduct , enantioselective synthesis , catalysis , alkyl , silane
Denmark’s chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base‐Lewis acid catalyst for the vinylogous 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 δ‐hydroxylated γ‐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 ‐configured adducts prevailing when furan‐ or N ‐alkyl/alkenylpyrrole donors are involved.