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Volumn 322, Issue 5898, 2008, Pages 77-80

Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; IMIDAZOLIDINE DERIVATIVE;

EID: 53349122064     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1161976     Document Type: Article
Times cited : (1944)

References (31)
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    • P. Renaud, M. P. Sibi, Eds, Wiley-VCH, Weinheim, Germany
    • P. Renaud, M. P. Sibi, Eds., Radicals in Organic Synthesis (Wiley-VCH, Weinheim, Germany, 2001).
    • (2001) Radicals in Organic Synthesis
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    • T. D. Beeson, A. Mastracchio, J. B. Hong, K. Ashton, D. W. C. MacMillan, Science 316, 582 (2007); published online 28 March 2007 (10.1126/science. 1142696).
    • T. D. Beeson, A. Mastracchio, J. B. Hong, K. Ashton, D. W. C. MacMillan, Science 316, 582 (2007); published online 28 March 2007 (10.1126/science. 1142696).
  • 9
    • 53349114531 scopus 로고    scopus 로고
    • A SOMO activation mechanism has also been reported for the a-oxidation of aldehydes (10).
    • A SOMO activation mechanism has also been reported for the a-oxidation of aldehydes (10).
  • 12
    • 53349137716 scopus 로고    scopus 로고
    • An intramolecular a-formyl alkylation has been reported 13
    • An intramolecular a-formyl alkylation has been reported (13).
  • 14
    • 53349093239 scopus 로고    scopus 로고
    • For a catalytic enantioselective alkylation of racemic α-bromoesters, see
    • For a catalytic enantioselective alkylation of racemic α-bromoesters, see (15).
    • , vol.15
  • 19
    • 53349149263 scopus 로고    scopus 로고
    • - electrode (20).
    • - electrode (20).
  • 21
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    • + has previously been shown to reduce phenacyl bromide (22).
    • + has previously been shown to reduce phenacyl bromide (22).
  • 24
    • 53349122437 scopus 로고    scopus 로고
    • The possibility of direct one-electron reduction of the α-bromocarbonyl by the α-amino radical as a propagation step cannot be excluded
    • The possibility of direct one-electron reduction of the α-bromocarbonyl by the α-amino radical as a propagation step cannot be excluded.
  • 25
    • 53349158559 scopus 로고    scopus 로고
    • DFT calculations were performed with the use of B3LYP/6-311+G(2d,2p)// B3LYP/6-31G(d).
    • DFT calculations were performed with the use of B3LYP/6-311+G(2d,2p)// B3LYP/6-31G(d).
  • 26
    • 53349083950 scopus 로고    scopus 로고
    • A conformer that positions the enamine olefin toward the tert-butyl group was also found to be energetically relevant in these calculations. Because of the pseudo C2-symmetric nature of catalyst 6, this enamine conformer also exists with the Si face open and the Re face blocked in a manner similar to DFT-8.
    • A conformer that positions the enamine olefin toward the tert-butyl group was also found to be energetically relevant in these calculations. Because of the pseudo C2-symmetric nature of catalyst 6, this enamine conformer also exists with the Si face open and the Re face blocked in a manner similar to DFT-8.
  • 27
    • 53349114529 scopus 로고    scopus 로고
    • Materials and methods are available as supporting material on Science Online.
    • Materials and methods are available as supporting material on Science Online.
  • 28
    • 53349136643 scopus 로고    scopus 로고
    • 4NCl.
    • 4NCl.
  • 30
    • 53349083951 scopus 로고    scopus 로고
    • 2+.
    • 2+.
  • 31
    • 53349086009 scopus 로고    scopus 로고
    • We thank S. Bernhard for his assistance in performing quenching experiments, as well as many insightful discussions. Additionally, we thank T. J. Rainey for performing DFT calculations. Financial support was provided by the NIH General Medical Sciences (grant R01 GM078201-01-01) and gifts from Merck, Amgen, and Bristol-Myers Squibb. D.A.N. is grateful for a NIH National Service Research Award fellowship F32GM076816
    • We thank S. Bernhard for his assistance in performing quenching experiments, as well as many insightful discussions. Additionally, we thank T. J. Rainey for performing DFT calculations. Financial support was provided by the NIH General Medical Sciences (grant R01 GM078201-01-01) and gifts from Merck, Amgen, and Bristol-Myers Squibb. D.A.N. is grateful for a NIH National Service Research Award fellowship (F32GM076816).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.