Ammonia → (1S)-2-amino-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

Participants

Reaction Steps

Epoxide 22 was prepared (Y. L. Merrer et al., Tetrahed. Lett. 1988, 31, 1003; M. Pottie et al. 1991, 2, 329; A. H. Al-Hakim et al., Synthesis, 1985, 207) from inexpensive and enantiomerically pure D-isoascorbic acid. The epoxide was dissolved in a large excess of methanol and added to a large volume of a saturated solution of ammonia in methanol and allowed to stand for 24 hr. The solvent was evaporated to afford the aminoalcohol 23.

Provenance & Evidence