Lipase-mediated resolution of 4-TMS-3-butyn-2-ol and use of the mesylate derivatives as a precursor to a highly stereoselective chiral allenylindium reagent

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3369-3372

  Marshall, James A ^a   Chobanian, Harry R ^a   Yanik, Mathew M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 TRIMETHYLSILYL 3 BUTYN 2 OL; 4-TRIMETHYLSILYL-3-BUTYN-2-OL; ALKYNE; BUTANOL; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MESYLIC ACID DERIVATIVE; PROPANOL; PROPARGYL ALCOHOL; TRIACYLGLYCEROL LIPASE; TRIMETHYLSILYL DERIVATIVE;

ACETYLATION; ARTICLE; CHEMISTRY; LIQUID CHROMATOGRAPHY; METABOLISM; METHODOLOGY; STEREOISOMERISM; TECHNIQUE;

ACETYLATION; ALKYNES; BUTANOLS; CHROMATOGRAPHY, LIQUID; INDICATORS AND REAGENTS; LIPASE; MESYLATES; METHODS; PROPANOLS; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 0035909596     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016605x     Document Type: Article

References (22)

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12. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129. For an application of the lipase resolution methodology to (E)-4-diphenyl-silyl-3-buten-2-ol and 4-diphenylsilyl-3-butyn-2-ol, see, respectively: Beresis, R. T.; Solomon, J. S.; Yang, M. G.; Jain, N. F.; Panek, J. S. Org. Synth. 1997, 75, 78. Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323.
13. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129. For an application of the lipase resolution methodology to (E)-4-diphenyl-silyl-3-buten-2-ol and 4-diphenylsilyl-3-butyn-2-ol, see, respectively: Beresis, R. T.; Solomon, J. S.; Yang, M. G.; Jain, N. F.; Panek, J. S. Org. Synth. 1997, 75, 78. Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323.
14. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129. For an application of the lipase resolution methodology to (E)-4-diphenyl-silyl-3-buten-2-ol and 4-diphenylsilyl-3-butyn-2-ol, see, respectively: Beresis, R. T.; Solomon, J. S.; Yang, M. G.; Jain, N. F.; Panek, J. S. Org. Synth. 1997, 75, 78. Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323.
15. Chiral allenylpalladium compounds are racemized by Pd(O) catalysts. Elsevier, C. J.; Vermeer, P. J. Org. Chem. 1985, 50, 3042.
16. See also: Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
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20. Support for the eclipsed transition states has been obtained for the analogous allenylzinc additions through ab initio calculations at the 3-21G* basis set level. Details of these calculations will be described in a forthcoming publication.
21. Cf. Nishihara, Y.; Ikegashira, K.; Hirabayashi, K. Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. Results from our laboratory will be described in a forthcoming publication.
22. 2. GC analysis of the crude acetate on a β-Dex column indicated a 97:3 enantiomeric ratio.