Vanadium-catalyzed addition of propargyl alcohols and imines

Journal of the American Chemical Society

Volumn 128, Issue 32, 2006, Pages 10358-10359

  Trost, Barry M ^a   Chung, Cheol K ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; IMINE; PROPARGYL ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; ELECTRON TRANSPORT; ENANTIOMER; MANNICH REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STOICHIOMETRY; TRANSESTERIFICATION;

ALKYNES; CATALYSIS; IMINES; MOLECULAR STRUCTURE; PROPANOLS; VANADIUM;

EID: 33747603699     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064011p     Document Type: Article

References (13)

1. (a) Trost, B. M. Science 1991, 254, 1471.
2. (b) Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259.
3. For propargyl alcohol reactions, see: (a) Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230.
4. For allenic alcohol reactions, see: (b) Trost, B. M.; Jonasson, C.; Wucher, M. J. Am. Chem. Soc. 2001, 123, 12736.
5. (c) Trost, B. M.; Jonasson, C. Angew. Chem., Int. Ed. 2003, 42, 2063.
6. (a) Meyer, K. H.; Schuster, K. Chem. Ber. 1922, 55, 819.
7. (b) Swaminat, S.; Narayana, K. V. Chem. Rev. 1971, 71, 429.
8. Pauling, H.; Andrews, D. A.; Hindley, N. C. Helv. Chim. Acta 1976, 59, 1233.
9. The imines were prepared according to (a) Kupfer, R.; Meier, S.; Wurthwein, E. U. Synthesis 1984, 688.
10. Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
11. Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
12. The nearly complete racemization indicates that the rearrangement may proceed through an ion-pair intermediate involving a propargylic cation, instead of a cyclic transition state. For a similar nonstereospecific oxometal-catalyzed transformation, see: Sherry, B. D.; Radosevich, A. T.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 6076.
13. Shi, Y. L.; Xu, Y. M.; Shi, M. Adv. Synth. Catal. 2004, 346, 1220.