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Volumn 20, Issue 21, 2009, Pages 2421-2427

Dynamic resolution of α-halo carboxylic acid derivatives in asymmetric nucleophilic substitution using chiral auxiliaries

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBOXYLIC ACID DERIVATIVE; HALOGEN; NITROGEN DERIVATIVE; NUCLEOPHILE; OXYGEN DERIVATIVE;

EID: 72049084488     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.10.014     Document Type: Review
Times cited : (15)

References (69)
  • 10
    • 72049109882 scopus 로고    scopus 로고
    • note
    • It has been proposed that the epimerization of α-halo carbon center is promoted via the nucleophilic displacement of the halide ion and/or base-catalyzed keto-enol tautomerization process.
  • 18
    • 27944472739 scopus 로고    scopus 로고
    • When chiral auxiliary bound α-halo acid derivative 1 was prepared from racemic α-halo carboxylic acid, we might expect to obtain a 1:1 diastereomeric mixture of 1. In some cases, however, the formation of anything other than a 1:1 mixture of diastereomers is observed, which can be explained by dynamic resolution in the ester or amide bond formation reaction. Also, the in situ preparation of a ketene from α-halo acid halides and its asymmetric reaction with a chiral auxiliary can afford α-halo esters or amides with high stereoselectivities:
    • When chiral auxiliary bound α-halo acid derivative 1 was prepared from racemic α-halo carboxylic acid, we might expect to obtain a 1:1 diastereomeric mixture of 1. In some cases, however, the formation of anything other than a 1:1 mixture of diastereomers is observed, which can be explained by dynamic resolution in the ester or amide bond formation reaction. Also, the in situ preparation of a ketene from α-halo acid halides and its asymmetric reaction with a chiral auxiliary can afford α-halo esters or amides with high stereoselectivities:. Boschi F., Camps P., Comes-Franchini M., Muňoz-Torrero D., Ricci A., and Sánchez L. Tetrahedron: Asymmetry 16 (2005) 3739
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3739
    • Boschi, F.1    Camps, P.2    Comes-Franchini, M.3    Muňoz-Torrero, D.4    Ricci, A.5    Sánchez, L.6
  • 28
    • 72049125013 scopus 로고    scopus 로고
    • We have performed molecular mechanics calculations (MMC) with the InsightII/Discover program using consistent valence force field, unpublished results.
    • We have performed molecular mechanics calculations (MMC) with the InsightII/Discover program using consistent valence force field, unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.