American Chemical Society
jo8b00586_si_003.cif (13.87 kB)

Access to β2‑Amino Acids via Enantioselective 1,4-Arylation of β‑Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

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posted on 2018-08-29, 00:00 authored by Jia-Hong Jian, Chih-Lung Hsu, Jin-Fong Syu, Ting-Shen Kuo, Ming-Kang Tsai, Ping-Yu Wu, Hsyueh-Liang Wu
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 β2-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β2-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.