Amino acid-based synthesis of trifluoromethylalkene dipeptide isosteres by alcohol-assisted nucleophilic trifluoromethylation and organozinc-copper- mediated SN2′ alkylation

Journal of Organic Chemistry

Volumn 74, Issue 12, 2009, Pages 4626-4629

  Kobayashi, Kazuya ^a   Narumi, Tetsuo ^a   Oishi, Shinya ^a   Ohno, Hiroaki ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIASTEREO-SELECTIVITY; DIPEPTIDE; DIPEPTIDE ISOSTERE; KETO ESTER; L-ALANINE; L-PHENYLALANINE; MESYLATES; NUCLEOPHILIC TRIFLUOROMETHYLATION; SYNTHETIC APPROACH; TRIFLUOROMETHYL GROUP;

ALKYLATION; AMINES; ESTERS; HYDROCARBONS; ORGANIC ACIDS; ORGANOMETALLICS;

AMINO ACIDS;

ALANINE; ALCOHOL; COPPER; DIPEPTIDE DERIVATIVE; ESTER; MESYLIC ACID; METHYL GROUP; NUCLEOPHILE; PHENYLALANINE; ZINC;

ARTICLE; CHEMICAL REACTION; METHYLATION; STEREOCHEMISTRY; SYNTHESIS;

ALANINE; ALKENES; ALKYLATION; AMINO ACIDS; COPPER; DIPEPTIDES; MESYLATES; ORGANOMETALLIC COMPOUNDS; PHENYLALANINE; ZINC;

EID: 67249158000     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9005602     Document Type: Article

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42. N2′ process and leads to the formation of a long-lived, isomerizable π-allyl copper complex. However, the steric effect would be more important to determine the diastereoselectivity because de values of trans-18 and 20 are dependent on the steric bulk of the copper reagents.
43. At present, removal of the Boc group and ester function without epimerization is difficult. For example, treatment of trans-18a (77% de) with 6 N HCl in AcOH at 100°C gave the corresponding deprotected isostere with 32% de in 90% yield (see the Supporting Information). Further investigation including preparation and deprotection of the tert-butyl ester will be necessary.