Access to β 2 -Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

Jia Hong Jian, Chih Lung Hsu, Jin Fong Syu, Ting Shen Kuo, Ming Kang Tsai, Ping Yu Wu, Hsyueh Liang Wu

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70% yields and >99.5% ee's, which are useful building blocks for preparing chiral β 2 -amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β 2 -amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.

Original languageEnglish
Pages (from-to)12184-12191
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number19
DOIs
Publication statusPublished - 2018 Oct 5

ASJC Scopus subject areas

  • Organic Chemistry

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