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本文报道了从(+)-樟脑与(+)或(—)-甘氨酸薄荷醇酯所得的亚胺3的烷基化反应,烷基化产物6经水解得到(R)-氨基酸7.与N-(特丁氧羰基亚甲基)-(+)-樟脑亚胺3c相比,由于存在匹配的双手性诱导效应,而使N-[甘氨酸-(+)-薄荷酯]-(+)-樟脑亚胺3a烷基化的立体选择性有明显的提高(43.8—98％),而不匹配的N-[甘氨酸-(—)-薄荷醇酯]-(+)-樟脑亚胺3b烷基化的立体选择性明显降低。3a和3b的甲基化都给出(S)-丙氨酸,且立体选择性不受薄荷酯的构型影响。
This paper reports the alkylation of imine 3 from (+) - camphor with (+) or (-) - glycine menthyl ester and hydrolysis of alkylated product 6 to give (R) - amino acid 7. Reaction with N - (+) - menthyl] - (+) - camphoric imine 3c due to the presence of a matching bipolar inducing effect, the N- (glycine- The stereoselectivity of camphane imine 3a alkylation was significantly improved (43.8-98%) while the unmatched N- [glycine- (-) - menthol ester] - The three-dimensional selectivity is significantly reduced. Methylation of 3a and 3b both gave (S) -alanine and the stereoselectivity was not affected by the configuration of the menthyl ester.