Addition of allenylzinc reagents, prepared in situ from nonracemic propargylic mesylates, to aldehydes. A new synthesis of highly enantioenriched homopropargylic alcohols

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5201-5204

  Marshall, James A ^a   Adams, Nicholas D ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; HOMOPROPARGYLIC ALCOHOL; MESYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033031265     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9823083     Document Type: Article

References (27)

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6. For a recent application, see: Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
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11. This combination has not previously been utilized. For a discussion of possible catalytically active species, see ref 5, p 2, and the following cited reference: Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
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15. 11 Full details are provided in the Supporting Information.
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19. E2′ additions. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 7. On the basis of other allenylmetal additions, we believe that the allyl analogy is appropriate. However, it should be noted that, under Barbier conditions, crotylzinc halides afford nearly 1:1 mixtures of anti and syn adducts, implying a rather loose transition state.
20. E2′ additions. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 7. On the basis of other allenylmetal additions, we believe that the allyl analogy is appropriate. However, it should be noted that, under Barbier conditions, crotylzinc halides afford nearly 1:1 mixtures of anti and syn adducts, implying a rather loose transition state.
21. E2′ additions. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 7. On the basis of other allenylmetal additions, we believe that the allyl analogy is appropriate. However, it should be noted that, under Barbier conditions, crotylzinc halides afford nearly 1:1 mixtures of anti and syn adducts, implying a rather loose transition state.
22. E2′ additions. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 7. On the basis of other allenylmetal additions, we believe that the allyl analogy is appropriate. However, it should be noted that, under Barbier conditions, crotylzinc halides afford nearly 1:1 mixtures of anti and syn adducts, implying a rather loose transition state.
23. Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364.
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25. Yadev, J. S.; Chandler, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455. Marshall, J. A.; Jiang, H. Tetrahedron Lett. 1998, 39, 1493. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
26. Yadev, J. S.; Chandler, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455. Marshall, J. A.; Jiang, H. Tetrahedron Lett. 1998, 39, 1493. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
27. Yadev, J. S.; Chandler, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455. Marshall, J. A.; Jiang, H. Tetrahedron Lett. 1998, 39, 1493. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.