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Volumn 51, Issue 27, 2012, Pages 6618-6621

A robust, efficient, and highly enantioselective method for synthesis of homopropargyl amines

Author keywords

copper; enantioselective catalysis; homopropargyl amines; N heterocyclic carbenes; propargyl additions

Indexed keywords

ALDIMINES; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; ENANTIOSELECTIVE CATALYSIS; HIGH ENANTIOSELECTIVITY; N-HETEROCYCLIC CARBENES; PROPARGYL;

EID: 84863207882     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202694     Document Type: Article
Times cited : (56)

References (35)
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    • For a review on catalytic enantioselective propargyl additions, see:, C.-H. Ding, X.-L. Hou, Chem. Rev. 2011, 111, 1914-1937.
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    • J. Chen, B. Captain, N. Takenaka, Org. Lett. 2011, 13, 1654-1657. Furthermore, in a recent study, homopropargyl amines were obtained as minor byproducts; see
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    • Chen, J.1    Captain, B.2    Takenaka, N.3
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    • For an example of catalytic enantioselective synthesis of propargyl glycine derivatives through the use of chiral-phase transfer catalysts, see:, S. L. Castle, G. S. C. Srikanth, Org. Lett. 2003, 5, 3611-3614.
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    • For an overview regarding the utility of N-phosphinoylimines in chemical synthesis, see:, S. M. Weinreb, R. K. Orr, Synthesis 2005, 1205-1227.
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    • Since protonation of the intermediate NHC-Cu-allene by MeOH does not constitute a major pathway, it is likely that N-phosphinoylimines are associated to the Lewis acidic transition metal when an NHC-Cu species is generated, leading to an intramolecular allyl transfer. Such considerations, together with the high levels of enantioselectivity, suggest that open transition structures are likely not involved. For a related discussion, see:, E. Vrancken, H. Gérard, D. Linder, S. Ouizem, N. Alouane, E. Roubineau, K. Bentayeb, J. Marrot, P. Mangeney, J. Am. Chem. Soc. 2011, 133, 10790-10802.
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    • Vrancken, E.1    Gérard, H.2    Linder, D.3    Ouizem, S.4    Alouane, N.5    Roubineau, E.6    Bentayeb, K.7    Marrot, J.8    Mangeney, P.9
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.