The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives

DOI: 10.1016/S0040-4020(01)90125-5

Source and publish data:

Tetrahedron p. 5163 - 5178 (1992)

Update date:2022-07-29

Topics:

Authors:

Hamon, David P. G.

Massy-Westropp, Ralph A.

Razzino, Pasquale

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Article abstract of DOI:10.1016/S0040-4020(01)90125-5

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.

Full text of DOI:10.1016/S0040-4020(01)90125-5

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