Anion reactions of strans-1,3-dithiolane 1,3-dioxide with aldehydes and comparison with trans-1,3-dithiane 1,3-kioxide

摘要

The reactions of metalated rans-1,3-dithiolane 1,3-dioxide (10) with aldehydes have been studied through variations in the metal conuterion, reaction temperature, and aldehyde. High yields of adducts were obtained, indicating that, in contrast to the monoxide or parent sulfide, the anion of 1,3-dithiolane 1,3-dioxide was sufficiently stable and did not decompose. High diastereoselectivities were obtained under kinetically controlled conditions, using an excess of lithium base at -78 deg C.