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.
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 beta-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.
Lei
Aiwen
A
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Liu
Guosheng
G
Lu
Xiyan
X