Novel and practical asymmetric synthesis of β2, 3-amino esters using asymmetric Michael addition of chiral amine. Issue 15 (13th April 2017)

• Record Type: Journal Article
• Authors: Ozeki, Minoru; Egawa, Honoka; Takano, Toshiki; Mizutani, Hideki; Yasuda, Narumi; Arimitsu, Kenji; Kajimoto, Tetsuya; Hosoi, Shinzo; Iwasaki, Hiroki; Kojima, Naoto; Node, Manabu; Yamashita, Masayuki
• Is Part Of: Tetrahedron. Volume 73:Issue 15(2017)
• Page Start: 2014
• Page End: 2021
• Publication Date: 2017-04-13
• Subjects: β2, 3-Amino acid -- Asymmetric Michael addition -- Face-selective protonation -- Chiral amine -- Trisubstituted (E)-α, β-unsaturated ester; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.02.037
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A practical method for the synthesis of chiral β 2, 3 -amino esters having various substituents was developed, which is characterized by an asymmetric Michael addition reaction of a chiral lithium amide with trisubstituted ( E )-α, β-unsaturated esters. We found that a highly face-selective protonation occurred by the quick addition of water to the enolate intermediate derived from the Michael addition reaction to afford N -protected β 2, 3 -amino esters in moderate to excellent yields. This finding was made possible by the facile preparation of geometrically pure trisubstituted ( E )-α, β-unsaturated esters, which was established recently by our group. The subsequent deprotection of the amino group in the Michael adduct by using N -iodosuccinimide (NIS) efficiently provided β 2, 3 -amino esters having various substituents. Graphical abstract: