Russian Chemical Bulletin p. 917 - 923 (1999)
Update date:2022-07-30
Topics:
Belokon'
Kochetkov
Churkina
Ikonnikov
Chesnokov
Larionov
Kagan
It is shown that sodium alkoxides formed from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethanol) ((R,R)-TADDOL) and some of its derivatives can be used as chiral catalysts for enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α-methytphenyl-alanine, (R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61-93% yields and with ee 69-94%. When (S,S)-TADDOL is used, the (3)-amino acid is formed. A mechanism explaining the observed features of the reaction is proposed.
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Doi:10.1248/cpb.47.1053
(1999)Doi:10.1016/S0022-328X(99)00215-6
(1999)Doi:10.1021/jo900180p
(2009)Doi:10.1016/S0020-1693(00)83225-9
(1989)Doi:10.1016/s0020-1693(99)00105-x
(1999)Doi:10.1002/(SICI)1099-1344(199909)42:9<835::AID-JLCR244>3.0.CO;2-R
(1999)
