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Organocatalytic Enantioselective Conia‐Ene‐Type Carbocyclization of Ynamide Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans
Author(s) -
Xu Yin,
Sun Qing,
Tan TongDe,
Yang MingYang,
Yuan Peng,
Wu ShaoQi,
Lu Xin,
Hong Xin,
Ye LongWu
Publication year - 2019
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.201908495
Subject(s) - cycloisomerization , enantioselective synthesis , chemistry , regioselectivity , substrate (aquarium) , ene reaction , stereochemistry , organocatalysis , combinatorial chemistry , catalysis , organic chemistry , biology , ecology
Described herein is an organocatalytic enantioselective desymmetrizing cycloisomerization of arylsulfonyl‐protected ynamide cyclohexanones, representing the first metal‐free asymmetric Conia‐ene‐type carbocyclization. This method allows the highly efficient and atom‐economical construction of a range of valuable morphans with wide substrate scope and excellent enantioselectivity (up to 97 % ee ). In addition, such a cycloisomerization of alkylsulfonyl‐protected ynamide cyclohexanones can lead to the divergent synthesis of normorphans as the main products with high enantioselectivity (up to 90 % ee ). Moreover, theoretical calculations are employed to elucidate the origins of regioselectivity and enantioselectivity.
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