Journal
ORGANIC LETTERS
Volume 20, Issue 4, Pages 1142-1145Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00072
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Funding
- Qingdao University
- National Natural Science Foundation of China [21502043]
- Natural Science Foundation of Shandong Province [ZR2017JL011]
- Special Funds for the Development of Strategic Emerging Industries in Shenzhen [VJCYJ20160429191918729]
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This work describes the first enantioselective 1,6-additions of azlactones to para-quinone methides. In the presence of a chiral phosphoric acid, 1,6-adducts were obtained in high yields (up to 96%) with excellent diastereoselectivities and enantioselectivities (all >20:1 dia-stereoselectivity ratio (dr), up to 99% enantiomeric excess (ee)). Importantly, the method offers a facile synthetic approach, not only to enantiopure alpha,alpha-disubstituted alpha-amino acid esters, but also to unnatural enantioenriched beta,beta-diaryl-alpha-amino acid esters bearing adjacent tertiary and quaternary stereogenic centers.
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