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Volumn , Issue 33, 2007, Pages 5487-5491

A temporary stereocentre approach for the stereodivergent synthesis of either enantiomer of α-methyloctanal

Author keywords

Aldol; Chiral aldehyde; Hydrogenation; retro Aldol reaction; Temporary stereocentre

Indexed keywords


EID: 36348939278     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700782     Document Type: Article
Times cited : (11)

References (35)
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    • For a discussion of the potential benefits of 5,5-dimethyloxazolidin-2- ones (SuperQuats) see: a) S. D. Bull, S. G. Davies, S. Jones, H. J. Sanganee, J. Chem. Soc. Perkin Trans. 1 1999, 387-398;
    • For a discussion of the potential benefits of 5,5-dimethyloxazolidin-2- ones (SuperQuats) see: a) S. D. Bull, S. G. Davies, S. Jones, H. J. Sanganee, J. Chem. Soc. Perkin Trans. 1 1999, 387-398;
  • 8
    • 0042735337 scopus 로고    scopus 로고
    • syn-Aldols 6 and 8 were prepared using our previously reported protocols, see: a F. J. P. Feuillet, D. E. J. E. Robinson, S. D. Bull, Chem. Commun. 2003, 2184-2185;
    • syn-Aldols 6 and 8 were prepared using our previously reported protocols, see: a) F. J. P. Feuillet, D. E. J. E. Robinson, S. D. Bull, Chem. Commun. 2003, 2184-2185;
  • 13
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    • [6]).
    • [6]).
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    • [6]).
    • [6]).
  • 15
    • 36348966277 scopus 로고    scopus 로고
    • 4 stereocentres of all (4S)- and (4R)-aldols were assigned from the sign of the specific rotation of the (R)- or (S)-α-methyloctanal (14) generated from their retro-aldol cleavage, as well as from the identity of the major imidazolidine diastereoisomer formed from its derivatization with (S,S)-DMPEDA.
    • 4 stereocentres of all (4S)- and (4R)-aldols were assigned from the sign of the specific rotation of the (R)- or (S)-α-methyloctanal (14) generated from their retro-aldol cleavage, as well as from the identity of the major imidazolidine diastereoisomer formed from its derivatization with (S,S)-DMPEDA.
  • 17
    • 0037160423 scopus 로고    scopus 로고
    • anti-Aldols 10 and 12 were prepared according to the protocol previously described by D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392-393.
    • anti-Aldols 10 and 12 were prepared according to the protocol previously described by D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392-393.
  • 19
    • 84982361666 scopus 로고    scopus 로고
    • For previous reports on the asymmetric syntheses of (S)- or (R)-α-methyloctanal in varying ee values, see: a) G. Consiglio, C. Botteghi, C. Salomon, P. Pino, Angew. Chem. Int. Ed. Engl. 1973, 12, 669-670;
    • For previous reports on the asymmetric syntheses of (S)- or (R)-α-methyloctanal in varying ee values, see: a) G. Consiglio, C. Botteghi, C. Salomon, P. Pino, Angew. Chem. Int. Ed. Engl. 1973, 12, 669-670;
  • 27
    • 36348973147 scopus 로고    scopus 로고
    • The enantiomeric excesses of (R)- and (S)-α- methyloctanal (14) produced in these retro-aldol reactions were determined by derivatisation with (S,S)-DMEPDA.
    • The enantiomeric excesses of (R)- and (S)-α- methyloctanal (14) produced in these retro-aldol reactions were determined by derivatisation with (S,S)-DMEPDA.
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    • For related Wittig homologations of masked aldehyde equivalents see: a
    • For related Wittig homologations of masked aldehyde equivalents see: a) D. J. Dixon, M. S. Scott, C. A. Luckhurst, Synlett 2005, 2420-2424;
    • (2005) Synlett , pp. 2420-2424
    • Dixon, D.J.1    Scott, M.S.2    Luckhurst, C.A.3
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    • Although the α,β-unsaturated ester (E,R)-18 has not been reported previously, Wittig homologation of related chiral α-alkyl aldehydes are known to proceed with no loss of enantiopurity; See: a) R. Baker, J. C. Head, C. J. Swain, J. Chem. Soc. Perkin Trans. 1 1988, 85-97;
    • Although the α,β-unsaturated ester (E,R)-18 has not been reported previously, Wittig homologation of related chiral α-alkyl aldehydes are known to proceed with no loss of enantiopurity; See: a) R. Baker, J. C. Head, C. J. Swain, J. Chem. Soc. Perkin Trans. 1 1988, 85-97;
  • 35
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    • 3); See: A. G. Jamieson, A. Sutherland, Org. Biomol. Chem. 2005, 3, 735-736.
    • 3); See: A. G. Jamieson, A. Sutherland, Org. Biomol. Chem. 2005, 3, 735-736.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.