Stereoselective Synthesis of (-)-α-Conhydrine and Its Pyrrolidine Analogue

The stereoselective synthesis of (–)-α-conhydrine and its pyrrolidine analogue was achieved from readily available D-erythronolactone. The key step of this synthesis includes a highly regioselective and diastereoselective addition of chlorosulfonyl isocyanate to 1,2-anti-dibenzyl ether to afford the 1,2-anti-amino alcohol.