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Lewis Acid‐Catalyzed Stereoselective α‐Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides
Author(s) -
Adamkiewicz Anna,
Węglarz Izabela,
Butkiewicz Aleksandra,
Woyciechowska Marta,
Mlynarski Jacek
Publication year - 2020
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.201901218
Subject(s) - chemistry , silanes , stereoselectivity , aldol reaction , lewis acids and bases , catalysis , organic chemistry , furan , silane
The stereoselective α‐addition to cyclic dienol silanes has rarely been exploited, in contrast to the well‐studied γ‐addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α‐addition of 2‐trimetylsiloxy furan to optically pure aldehydes in water‐containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural products: vitexolide D, curcucomosin C, villosin, chinensine C, (+)‐coronarin E and ( E )‐labda‐7,11,13‐trien‐16,15‐olid.