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Volumn 39, Issue 7, 2000, Pages 1323-1325

Enantioselective β-amino acid synthesis based on catalyzed asymmetric acyl halide-aldehyde cyclocodensation reactions

Author keywords

Aluminum; Amino acids; Asymmetric catalysis; Lactones; Nucleophilic additions

Indexed keywords

ACID HALIDE; ALDEHYDE; BETA AMINO ACID; LACTONE;

EID: 0034599875     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000403)39:7<1323::AID-ANIE1323>3.0.CO;2-X     Document Type: Article
Times cited : (58)

References (43)
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    • Asymmetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: a) Reference [1];
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    • β-Lactones possessing α-branched substituents are not obtained in sufficiently high enantioselectivities from the catalyzed AAC reactions to be generally useful. Lactone 1g was readily prepared from the enzyme-mediated resolution of the racemic β-lactone that was derived from the achiral AAC reaction, see: a) S. G. Nelson, K. L. Spencer, J. Org. Chem. 2000, 65, 1227-1230: see also:
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    • note
    • 3M). The configuration of the remaining β-azido acids (4a,f,g) was assigned by analogy to these determinations.
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    • note
    • To verify that lactone ring opening was proceeding with rigorous inversion of configuration, the enantiomeric purities of azides 4a-c were determined by chiral-phase HPLC (Chiralcel OD-H column) of the methyl esters derived from 4a and 4b, and the benzyl ester derived from 4c.
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    • note
    • 3, DMF) followed by coupling the derived β-amino ester with (S)-α-methoxyphenylacetic acid (dicyclohexyl carbodiimide, 5 mol% 4-(dimethylamino)pyridine).
  • 42
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    • note
    • Attempts to introduce carbamale-protected nitrogen residues by addition of benzylcarhamate- or tert-butylcarbamate-derived anions afforded β-hydroxy imide products derived from predominant carbonyl addition.
  • 43
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    • note
    • 3, DMF) of representative β-sulfonamido esters 8 proceeded in 80-90% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.