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 | Zendy

Yu Zhipeng | Zendy; Liu Xiaohua | Zendy; Dong Zhenhua | Zendy; Xie Mingsheng | Zendy; Feng Xiaoming | Zendy

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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.

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