2. Academic Validation
  3. Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone

Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone

  • Org Lett. 2011 Jun 17;13(12):3056-9. doi: 10.1021/ol200939t.
Lin Zhou 1,  Lili Lin,  Jie Ji,  Mingsheng Xie,  Xiaohua Liu,  Xiaoming Feng
Affiliations

Affiliation

  • 1 Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
PMID: 21595425 DOI: 10.1021/ol200939t
Abstract

A direct highly diastereo- and enantioselective asymmetric vinylogous Mannich-type (AVM) reaction of aldimines with nonactivated natural α-angelica lactone has been successfully developed. It was demonstrated that the nonactivated natural α-angelica lactone is a useful vinylogous nucleophile to give the chiral δ-amino γ,γ-disubstituted butenolide carbonyl derivatives. The N,N'-dioxide L2-Sc(III) complex is efficient toward the obtention of a range of corresponding products with adjacent quaternary and tertiary stereocenters in excellent dr and ee values.

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