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Diastereo‐ and Enantioselective Synthesis of trans ‐2,3‐Disubstituted 2,3‐Dihydropyran‐4‐one Derivatives
Author(s) -
Scettri Arrigo,
Acocella Maria R.,
Palombi Laura,
Scalera Chiara,
Villano Rosaria,
Massa Antonio
Publication year - 2006
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.200606159
Subject(s) - chemistry , enantioselective synthesis , diene , dihydropyran , aldol reaction , enantiomer , lewis acids and bases , stereochemistry , derivative (finance) , activator (genetics) , organic chemistry , catalysis , biochemistry , natural rubber , financial economics , economics , gene
trans ‐Diastereoselective hetero‐Diels–Alder reactions took place in the presence of SiCl 4 /activator systems. The reactions of aldehydes with a derivative of Danishefsky’s diene afforded the corresponding pyrones with high yields and diastereoselectivity upon activating SiCl 4 with suitable neutral Lewis bases. Aldol intermediates deriving from a Mukaiyama‐type pathway were isolated in many cases. The employment of a chiral activator allowed us to convert Danishefsky’s diene (or its disubstituted derivative) into both aldols and pyrones in good to high enantiomeric excesses.