Asymmetric synthesis of [2,3-C-13(2), N-15]-4-benzyloxy-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazine-2-one via lipase TL-mediated kinetic resolution ofbenzoin: General procedure for the synthesis of [2,3-C-13(2),N-15]-L-alanine
Y. Aoyagi et al., Asymmetric synthesis of [2,3-C-13(2), N-15]-4-benzyloxy-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazine-2-one via lipase TL-mediated kinetic resolution ofbenzoin: General procedure for the synthesis of [2,3-C-13(2),N-15]-L-alanine, J ORG CHEM, 66(24), 2001, pp. 8010-8014
Lipase TL-mediated kinetic resolution of benzoin proceeded to give the corr
esponding optically pure (R)-benzoin (R)-1. On the other hand, (S)-benzoin
O-acetate (S)-7 could be hydrolyzed without epimerization to give (S)-benzo
in (S)-1 under alkaline conditions. Furthermore, both enantiomers of benzoi
n (1) were converted to [N-15]-(1R,2S)- and (1S,2R)- 2-amino-1,2-diphenylet
hanol (3a and 3b), respectively, according to the procedure reported previo
usly. [2,3-C-13(2),N-15]-(5S,6R)-4-benzyloxy5,6-diphenyl-2,3,5,6-tetrahydro
-4H-oxazine-2-one (10) was synthesized from ethyl [1,2-C-13(2)]-bromoacetat
e and (1R,2S)-2-amino-1,2-diphenylethanol (3b) in three steps. Finally, [2,
3-C-13(2), 15N]-L-alanine (12) was prepared via alkylation of the lactone 1
0 and hydrogenation of the alkylated product 11.