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Volumn 7, Issue 17, 2009, Pages 3537-3548

A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC SYNTHESIS; CHIRAL AUXILIARIES; CYCLOPROPANATION; CYCLOPROPYL; ENANTIOPURE; ENOLATES; GOOD YIELD; LITHIUM ALKOXIDES; NATURAL PRODUCTS; OXAZOLIDIN-2-ONES; STEP SEQUENCES; SYN-ALDOLS; UNSATURATED ALDEHYDES;

EID: 70349298428     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b908600e     Document Type: Article
Times cited : (25)

References (141)
  • 91
    • 0033104486 scopus 로고    scopus 로고
    • 1H NMR spectra of crude reaction products revealed no evidence of competing formation of any oxazinane-2,4-dione or (E)-amide products in these reactions These conditions have also been used previously for asymmetric syn-aldol reactions using imidazolidin-2-one derived glycine enolates, see:
    • S. G. Davies H. J. Sanganee P. Szolcsanyi Tetrahedron 1999 55 3337
    • (1999) Tetrahedron , vol.55 , pp. 3337
    • Davies, S.G.1    Sanganee, H.J.2    Szolcsanyi, P.3
  • 93
    • 0002525102 scopus 로고
    • For a previous example of a syn-aldol reaction between an N-acyl-oxazolidin-2-one and an alkyn-2-al, see:
    • E. J. Corey S. Terashima Tetrahedron Lett. 1972 13 1815
    • (1972) Tetrahedron Lett. , vol.13 , pp. 1815
    • Corey, E.J.1    Terashima, S.2
  • 98
    • 0029019601 scopus 로고
    • For a discussion on the mechanism of directed cyclopropanation reactions of allylic alcohols, see:
    • A. B. Charette H. Lebel J. Org. Chem. 1995 60 2966
    • (1995) J. Org. Chem. , vol.60 , pp. 2966
    • Charette, A.B.1    Lebel, H.2
  • 119
    • 0035828834 scopus 로고    scopus 로고
    • For examples of epimerisation of cis-1,2-dimethyl esters of cyclopropanes to their more stable trans-diastereoisomers see:
    • W. Donaldson Tetrahedron 2001 57 8589
    • (2001) Tetrahedron , vol.57 , pp. 8589
    • Donaldson, W.1
  • 134
    • 85057635765 scopus 로고    scopus 로고
    • Treatment of syn-aldol 32 with 1.1 equivalents of LHMDS in THF at -40 °C resulted in a slower retro-aldol cleavage reaction which resulted in cyclopropane-carboxaldehyde 5i being obtained in a lower 74% yield due to more extensive enolate decomposition For related approaches see:
    • R. Green A. T. Merritt S. D. Bull Chem. Commun. 2008 508
    • (2008) Chem. Commun. , pp. 508
    • Green, R.1    Merritt, A.T.2    Bull, S.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.