The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Jan. 28, 2014

Filed:

Sep. 17, 2012
Applicants:

Samuel Helmer Gellman, Madison, WI (US);

Yonggui Chi, Berkeley, CA (US);

LI Guo, Madison, WI (US);

Inventors:

Samuel Helmer Gellman, Madison, WI (US);

Yonggui Chi, Berkeley, CA (US);

Li Guo, Madison, WI (US);

Assignee:
Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07C 231/04 (2006.01); C07C 269/04 (2006.01); C07C 227/12 (2006.01); C07C 271/22 (2006.01); C07C 227/02 (2006.01); C07C 269/00 (2006.01);
U.S. Cl.
CPC ...
C07C 271/22 (2013.01); C07C 227/02 (2013.01); C07C 269/00 (2013.01);
Abstract

The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide α-substituted-γ-nitroaldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96-99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to protected γ-amino acids, which are essential for systematic conformational studies of γ-peptide foldamers.


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