Asymmetric Synthesis of Functionalized Bicyclic β-Amino Alcohols by Cascade Hydrometallation-Cyclization-Reduction of Glycinyl-Substituted Alkenylsulfox­imines - Application to the Synthesis of an Aggrecanase Inhibitor Mimic

2011 ◽  
Vol 2011 (30) ◽  
pp. 5991-6008 ◽  
Author(s):  
Serdar Acikalin ◽  
Gerhard Raabe ◽  
Jan Runsink ◽  
Hans-Joachim Gais
Keyword(s):  
Asymmetric Synthesis ◽  
Amino Alcohols

Chiral β-Amino Alcohols and Derivatives in the Asymmetric Synthesis of Tetrahydroisoquinolines

ChemInform ◽  
2004 ◽  
Vol 35 (31) ◽  
Author(s):  
Eneritz Anakabe ◽  
Dolores Badia ◽  
Luisa Carrillo ◽  
Efraim Reyes ◽  
Jose L. Vicario
Keyword(s):  
Asymmetric Synthesis ◽  
Amino Alcohols

Highly Diastereoselective Oxy-Michael Additions of Enantiopureδ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

2003 ◽  
Vol 115 (35) ◽  
pp. 4373-4376 ◽  
Author(s):  
Nicola J. Adderley ◽  
David J. Buchanan ◽  
Darren J. Dixon ◽  
Dramane I. Lainé
Keyword(s):  
Asymmetric Synthesis ◽  
Amino Alcohols ◽  
Michael Additions

scholarly journals Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

2003 ◽  
Vol 75 (1) ◽  
pp. 39-46 ◽  
Author(s):  
J. A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Wide Range ◽  
Aldehydes And Ketones ◽  
Directing Group ◽  
High Yields ◽  
Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

Highly Diastereoselective Oxy-Michael Additions of Enantiopureδ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

2003 ◽  
Vol 42 (35) ◽  
pp. 4241-4244 ◽  
Author(s):  
Nicola J. Adderley ◽  
David J. Buchanan ◽  
Darren J. Dixon ◽  
Dramane I. Lainé
Keyword(s):  
Asymmetric Synthesis ◽  
Amino Alcohols ◽  
Michael Additions
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