(R)- and (S)-4-TIPS-3-butyn-2-ol. Useful precursors of chiral allenylzinc and indium reagents

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4840-4844

  Marshall, James A ^a   Eidam, Patrick ^a   Eidam, Hilary Schenck ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVITY; DIPHENYLETHYLENEDIAMINERUTHENIUM; DIPHENYLETHYLENEDIAMINERUTHENIUM CYMENE; ENANTIOSELECTIVITY;

ALCOHOLS; ALDEHYDES; IN SITU PROCESSING; INDIUM; MIXTURES; REDUCTION; ZINC;

PHENOLS;

4 TRIISOPROPYLSILYL 3 BUTYN 2 OL; ALCOHOL DERIVATIVE; ALLENYLZINC; ALPHA METHYL ALDEHYDE; ALPHA SILYLOXY ALDEHYDE; DIETHYLZINC; INDIUM; INDIUM IODIDE; IODIDE; KETONE; MESYLIC ACID DERIVATIVE; NOYORI N TOSYL 1,2 DIPHENYLETHYLENEDIAMINERUTHENIUM CYMENE; PHOSPHINE DERIVATIVE; REAGENT; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HOMOPROPARGYLIC ALCOHOL; PRECURSOR; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

ALKADIENES; BUTANOLS; CATALYSIS; INDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RUTHENIUM; SILANES; STEREOISOMERISM; ZINC;

EID: 33745466937     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060542k     Document Type: Article

References (35)

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20. Typical recent price listings: $155.50/g for (S)-3-butyn-2-ol and $114.00/g for (A)-3-butyn-2-ol.
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24. For an application of the lipase resolution methodology to (E)-4-(dimethylphenylsilyl)-3-buten-2-ol and 4-(dimethylphenylsilyl)-3-butyn-2- ol, see: Beresis, R. T.; Solomon, J. S.; Yang, M. G.; Jain, N. F.; Panek, J. S. Org. Synth. 1997, 75, 78.
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29. Preparation of the (R) enantiomer is described in the Supporting Information.
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31. 2Zn to heptenal and geranial take place in the absence of the propargylic mesylate but not in the absence of the palladium catalyst. We are currently examining this interesting addition reaction in detail to determine the scope and mechanism. For recent accounts of alkylzinc conjugate additions, see: Lipschutz, B. H.; Wood, M. R.; Tirando, R. J. Am. Chem. Soc. 1995, 117, 6126.
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35. A more detailed procedure for preparation of (R and S)-4-TIPS-butyn-2-ols has been submitted to Org. Synth.