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Enantioselective Synthesis of Highly Functionalized Phosphonate‐Substituted Pyrans or Dihydropyrans Through Asymmetric [4+2] Cycloaddition of β,γ‐Unsaturated α‐Ketophosphonates with Allenic Esters
Author(s) -
Pei ChengKui,
Jiang Yu,
Wei Yin,
Shi Min
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201206958
Subject(s) - enantioselective synthesis , phosphonate , cinchona , cycloaddition , chemistry , catalysis , dihydropyran , organic chemistry , organocatalysis , pyran
Tell me which you want : Catalytic asymmetric [4+2] cycloadditions of β,γ‐unsaturated α‐ketophosphonates with allenic esters catalyzed by organocatalysts derived from different cinchona alkaloids have been developed, affording phosphonate‐substituted functionalized pyran and dihydropyran derivatives in excellent yields with high enantioselectivities under mild conditions. The choice of product is controlled by the hydrogen bonding characteristics of the chosen catalyst.