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N-TFA-Gly-Bt-Based Stereoselective Synthesis of Substituted 3-Amino Tetrahydro-2H-pyran-2-ones via an Organocatalyzed Cascade Process

Author:
Han, Liuqing, Li, Ke, Xu, Haitong, Mei, Tao, Sun, Yali, Qu, Jingping, Song, Yuming
Source:
Journal of organic chemistry 2019 v.84 no.16 pp. 10526-10534
ISSN:
1520-6904
Subject:
aldehydes, catalytic activity, chemical reactions, chemical structure, enantioselectivity, organic chemistry, stereoselective synthesis
Abstract:
Chiral-substituted 3-amino tetrahydro-2H-pyran-2-ones were prepared in excellent enantioselectivities (up to 99% ee) via an organo-catalyzed cascade procedure with N-TFA-Gly-Bt and α,β-unsaturated aldehydes as the substrates. The corresponding tetrahydro-2H-pyran-2-ones can be used for further synthetic transformations that furnish chiral-substituted 3-aminopiperidin-2-ones with high levels of stereoselectivity.
Agid:
6571598