+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Enantioselective synthesis of α-fluoro-β(3)-amino esters: synthesis of enantiopure, orthogonally protected α-fluoro-β(3)-lysine



Enantioselective synthesis of α-fluoro-β(3)-amino esters: synthesis of enantiopure, orthogonally protected α-fluoro-β(3)-lysine



Journal of Organic Chemistry 75(21): 7365-7372



The scope of a tandem conjugate addition-fluorination sequence performed on α,β-unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(α-methylbenzyl)amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, α-fluoro-β(3)-amino esters can be obtained in up to quantitative yield and 80:20 to >99:1 dr. This simple methodology does not rely on the use of α-amino acids from the chiral pool and thus provides the potential for the preparation of enantiopure α-fluoro-β(3)-amino acids with a wide variety of side chains. Its utility was demonstrated through the synthesis of orthogonally protected (2S,3S)-α-fluoro-β(3)-lysine.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 052955090

Download citation: RISBibTeXText

PMID: 20931997

DOI: 10.1021/jo101600c


Related references

Stereoselective Synthesis of -Amino--Fluoro Esters via Diastereoselective Fluorination of Enantiopure -Amino Enolates. Synlett 5: 0791-0794, 2004

Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy. Journal of the American Chemical Society 2016, 2016

Asymmetric Michael addition of α-fluoro-α-nitro esters to nitroolefins: towards synthesis of α-fluoro-α-substituted amino acids. Organic and Biomolecular Chemistry 13(8): 2350-2359, 2015

Fluoroprostaglandins: synthesis and biological evaluation of the methyl esters of (+)-12-fluoro-, (-)-ent-12-fluoro-, (+)-15-epi-fluoro-, and (-)-ent-15 epi-12-fluoroprostaglandin F2 alpha. Journal of Medicinal Chemistry 23(10): 1072-1077, 1980

Fluoroprostaglandins: synthesis and biological evaluation of the methyl esters of (+)-12-fluoro-, (-)-ent-12-fluoro-, (+)-15-epi-fluoro-, and (-)-ent-15-epi-12-fluoroprostaglandin F2.alpha. Journal of Medicinal Chemistry 23(10): 1072-1077, 1980

Carbon-14 fluorinated prostaglandins: synthesis and biological evaluation of the methyl esters of (+)-14-fluoro-, (+)-15-epi-14-fluoro-, (+)-13(E)-14-fluoro-, and (+)-13(E)-15-epi-14-fluoroprostaglandin F2.alpha. Journal of Medicinal Chemistry 23(10): 1077-1083, 1980

Catalytic asymmetric mono-fluorination of α-keto esters: synthesis of optically active β-fluoro-α-hydroxy and β-fluoro-α-amino acid derivatives. Angewandte Chemie 51(19): 4581-4585, 2012

Synthesis of 3-amino-2,3,6-trideoxy-2-fluoro-L-talose and -D-allose [(R)-2-fluoro-L-daunosamine and (R)-2-fluoro-D-ristosamine. Carbohydrate Research 195(2): 225-245, 1990

Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation. Chemistry, An Asian Journal 10(2): 474-482, 2015

A Facile and Mild Approach for Stereoselective Synthesis of α-Fluoro-α,β-unsaturated Esters from α-Fluoro-β-keto Esters via Deacylation. Synlett 26(01): 127-132, 2014

Synthesis of benzyl and methyl 3-benzamido-2,3,6-trideoxy-2-fluoro-β-l-galactopyranoside: Protected C-2 fluoro analogues of daunosamine. Carbohydrate Research 140(1): 51-59, 1985

Synthesis of methyl 3-acetamido-4-O-benzoyl-2,3,6-trideoxy-2-fluoro-β-l-mannopyranoside: a protected 2-fluoro analogue of acosamine. Carbohydrate Research 152: 310-315, 1986

Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction. Chemical Communications 48(29): 3500-3502, 2012

Synthesis of methyl 3 acetamido 4 o benzoyl 2 3 6 trideoxy 2 fluoro beta l mannopyranoside a protected 2 fluoro analogue of acosamine. Carbohydrate Research 152: 312-315, 1986

Synthesis of -Fluoro-a, b-unsaturated Carboxylic Esters from Saturated a-Fluoro Aldehydes. Advanced Synthesis & Catalysis 342(1): 52-57, 2000