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Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol by Claudio Curti; Beatrice Ranieri; Lucia Battistini; Gloria Rassu; Vincenzo Zambrano; Giorgio Pelosi; Giovanni Casiraghi; Franca Zanardi is a Chemistry article available to read on EtoBox.

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## Abstract 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.

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

Author

Claudio Curti; Beatrice Ranieri; Lucia Battistini; Gloria Rassu; Vincenzo Zambrano; Giorgio Pelosi; Giovanni Casiraghi; Franca Zanardi

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley - V C H Verlag GmbbH & Co.; Wiley (ISSN 1615-4150)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)