Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates

Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates

A carbene-catalyzed enantioselective addition of enals to five-membered cyclic imines is developed. The reaction gives chiral quaternary α-amino phosphonates bearing tetrasubstituted carbon centers with excellent enantioselectivities. The imine substrates can be generated in situ from the correspond...

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Bibliographic Details
Main Authors: Sun, Jun, Mou, Chengli, Wang, Zhongyao, He, Fangcheng, Wu, Jian, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Journal Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Carbene-catalyzed
Enantioselective
Online Access:https://hdl.handle.net/10356/138289
Description
Summary:A carbene-catalyzed enantioselective addition of enals to five-membered cyclic imines is developed. The reaction gives chiral quaternary α-amino phosphonates bearing tetrasubstituted carbon centers with excellent enantioselectivities. The imine substrates can be generated in situ from the corresponding amines under an oxidative condition that is compatible with the carbene catalysis. Thus, a one-pot cross-dehydrogenative-coupling (CDC) reaction between enals and amines is also realized with high enantioselectivity remaining. The method provides quick enantioselective access to amino phosphonates with potential applications in medicines and pesticides.

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