Palladium(II)-Catalyzed Highly Regio- and Diastereoselective Cyclization of Difunctional Allylic N-Tosylcarbamates. A Convenient Synthesis of Optically Active 4-Vinyl-2-oxazolidinones and Total Synthesis of 1,4-Dideoxy-1,4-imino-l-xylitol
- 11 January 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (3) , 974-980
- https://doi.org/10.1021/jo0161429
Abstract
A Pd(II)-catalyzed cyclization of difunctional allylic N-tosyl carbamates in the presence of halide ions was developed with high regio- and diastereoselectivity. The reaction involves aminopalladation of alkene and β-heteroatom elimination to regenerate Pd(II) species. When the readily available homochiral alcohols were used as substrates, highly optically active 4-vinyl-2-oxazolidinones were easily obtained. The utility of this method was exemplified by the convenient synthesis of 1,4-dideoxy-1,4-imino-l-xylitol.Keywords
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