Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes: Preparation of 3-hydroxy-1-butynes

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4233-4236

  Boyall, D ^a   Lopez F ^a   Sasaki, H ^a   Frantz, D ^a   Carreira, E M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041780219     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006791r     Document Type: Article

References (16)

1. For some recent examples, see: (a) Fox, M. E.; Li, C.; Marino, J. P., Jr.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 5467.
2. (b) Trost, B. M.; Krische, M. J. J. Am. Chem. Soc. 1999, 121, 6131.
3. (c) Tan, L.; Chen, C.-Y.; Tillyer, R. D.; Grabowski, E. J. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711.
4. (d) Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995.
5. The Chemistry of Triple Bonded Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1983; Parts 1 and 2.
6. (a) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
7. (b) Carreira, E. M.; Singer, R. A. Drug Discovery Today 1996, 1, 145.
8. (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245;
9. (b) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806;
10. (c) Frantz, D. E.; Tomooka, C. S.; Fässler, R.; Carreira E. M. Accs. Chem. Res. 2000, 33, 373.
11. Carreira, E. M.; Sasaki, H. Unpublished results.
12. For catalytic, enantioselective additions of borylacetylides, see: (a) Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151. For the asymmetric addition of preformed bisalkynylzinc reagents to aryl ketones, see ref 1c.
13. For the preparation of propargylic alcohols by ynone reduction, see: (a) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
14. (b) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
15. Although there is precedence for the cleavage of acetone/alkyne adducts thermally (≈200°C), these examples are in general devoid of competing functionality in the substrate. The majority of acetone cleavage reactions have been performed on conjugated alkynes, see for example: (a) Inouye, M.; Hyodo, Y.; Nakazumi, H. J. Org. Chem. 1999, 64, 2704.
16. (b) Swindell, C. S.; Fan, W. J. Org. Chem. 1996, 61, 1109.