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DOI: 10.1055/s-2007-965989
Stereoselective Synthesis of Enantioenriched Acetylenic 1,2-Amino Alcohols
Publication History
Publication Date:
23 March 2007 (online)
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Abstract
The stereoselective synthesis of enantioenriched anti- and syn-4-aminoalk-1-yn-3-ols is described. Initial reaction of racemic 3-(methoxymethoxy)allenylzinc with enantiopure Ellman’s (S S)-(tert-butylsulfinyl)imines was shown to give straightforward and highly stereoselective access to anti-(S S,3S,4R)-3-(methoxymethoxy)-4-sulfinamidoalk-1-ynes. Upon treatment with dry methanolic hydrochloric acid at reflux, the latter led to the corresponding enantioenriched anti-(3S,4R)-4-aminoalk-1-yn-3-ols. Regarding the syn-diastereomeric (3R,4R)-4-aminoalk-1-yn-3-ols, they were obtained by ring opening of the corresponding cis-N-(tert-butylsulfinyl)aziridines by water under acidic conditions.
Key words
amino alcohols - asymmetric synthesis - chiral auxiliaries - sulfoxides - zinc
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