Thetert-Butanesulfinyl Group:  An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of β-Amino Acids

1999 ◽  
Vol 64 (1) ◽  
pp. 12-13 ◽  
Author(s):  
Tony P. Tang ◽  
Jonathan A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Directing Group

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.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2′,6′-dimethyl-tyrosines

1997 ◽  
Vol 38 (29) ◽  
pp. 5135-5138 ◽  
Author(s):  
Yinglin Han ◽  
Subo Liao ◽  
Wei Qiu ◽  
Chaozhong Cai ◽  
Victor J. Hruby
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Constrained Amino Acids

ChemInform Abstract: Asymmetric Synthesis via Heterocyclic Intermediates. Part 52. Synthesis of tert-Leucine and Related Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 24 (46) ◽  
pp. no-no
Author(s):  
U. GROTH ◽  
T. HUHN ◽  
B. PORSCH ◽  
C. SCHMECK ◽  
U. SCHOELLKOPF
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis

ChemInform Abstract: Asymmetric Synthesis of Trifluoromethyl-Piperidine Based γ-Amino Acids and of Trifluoromethyl-Indolizidines.

ChemInform ◽  
2013 ◽  
Vol 44 (24) ◽  
pp. no-no
Author(s):  
Wahid Bux Jatoi ◽  
Agnes Desiront ◽  
Aurelie Job ◽  
Yves Troin ◽  
Jean-Louis Canet
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis
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