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An N , N ′‐Dioxide/In(OTf) 3 Catalyst for the Asymmetric Hetero‐Diels–Alder Reaction Between Danishefsky's Dienes and Aldehydes: Application in the Total Synthesis of Triketide
Author(s) -
Yu Zhipeng,
Liu Xiaohua,
Dong Zhenhua,
Xie Mingsheng,
Feng Xiaoming
Publication year - 2008
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.200704759
Subject(s) - propionaldehyde , catalysis , yield (engineering) , chemistry , organic chemistry , medicinal chemistry , aldehyde , physics , thermodynamics
In‐teresting catalyst : An asymmetric hetero Diels–Alder reaction between Danishefsky's dienes and various aldehydes using an N , N ′‐dioxide/In(OTf) 3 complex affords highly substituted chiral dihydropyranones with up to 99 % ee (see scheme). The catalyst was applied to the synthesis of triketide from propionaldehyde in 72 % yield and with 97 % ee.