Tetrahedron p. 5163 - 5178 (1992)
Update date:2022-07-29
Topics:
Hamon, David P. G.
Massy-Westropp, Ralph A.
Razzino, Pasquale
The ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylgrycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.
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(1990)