Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines.

ChemInform ◽  
2004 ◽  
Vol 35 (19) ◽  
Author(s):  
Jared W. Evans ◽  
Jonathan A. Ellman
Keyword(s):  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Amino Alcohols

Direct Stereoselective Synthesis of Enantiomerically Pure anti-β-Amino Alcohols

2014 ◽  
Vol 79 (15) ◽  
pp. 6775-6782 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Osvaldo J. Donadel ◽  
Víctor S. Martín ◽  
José M. Padrón
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols ◽  
Enantiomerically Pure

Stereoselective synthesis of anti-2-oxazolidinones by Ph3P–CCl4–Et3N mediated SN2 cyclization of N-Boc-β-amino alcohols

2003 ◽  
Vol 44 (33) ◽  
pp. 6323-6325 ◽  
Author(s):  
G Madhusudhan ◽  
G Om Reddy ◽  
J Ramanatham ◽  
P.K Dubey
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols

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.

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