Asymmetric nucleophilic substitution of α-bromo amides via dynamic kinetic resolution for the preparation of dipeptide analogues

Tetrahedron

Volumn 60, Issue 30, 2004, Pages 6311-6318

  Nam, Jiyoun ^a   Chang, Ji Yeon ^a   Shin, Eun Kyoung ^a   Kim, Hyun Jung ^a   Kim, Yangmee ^a   Jang, Soonmin ^b   Park, Yong Sun ^a  

^a Konkuk University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

Asymmetric syntheses; Dipeptide; Dynamic kinetic resolution; Nucleophilic substitution; Peptidimimetics

Indexed keywords

AMIDE; DIBENZYLAMINE; DIPEPTIDE DERIVATIVE;

ARTICLE; ASYMMETRIC NUCLEOPHILIC SUBSTITUTION REACTION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DIASTEREOISOMER; DYNAMICS; EPIMER; HYDROGEN BOND; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 3242785709     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.094     Document Type: Article

References (26)

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18. The low selectivities in the absence of TBAI observed in entries 10 and 11, Table 2 suggest the possibility that the leaving group in the nucleophilic substitution in the presence of TBAI is iodide rather than bromide. Further mechanistic investigation for details of the process is underway
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