Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct mannich reaction under phase-transfer conditions

Organic Letters
Takashi OoiKeiji Maruoka

Abstract

[reaction: see text] Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C(2)-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

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Citations

Jan 26, 2006·Journal of the American Chemical Society·Susumu MitsumoriCarlos F Barbas
Mar 16, 2007·Chemical Communications : Chem Comm·Susumu SaitoShū Kobayashi
Jun 25, 2009·Chemical Society Reviews·Julien MichauxJean-Marc Campagne
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May 26, 2007·Angewandte Chemie·Takashi Ooi, Keiji Maruoka
Apr 4, 2009·Angewandte Chemie·Huy Van NguyenShū Kobayashi
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Oct 6, 2007·Chemical Reviews·Carmen Najera, José M Sansano
Aug 12, 2005·Chemical Reviews·Alma VisoAida Flores

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