Tetrahedron p. 1089 - 1098 (1980)
Update date:2022-08-28
Topics:
Belokon', Yu. N.
Zel'tzer, I. E.
Loim, N. M.
Tsiryapkin, V. A.
Aleksandrov, G. G.
et al.
1-(N,N-Dimethylaminomethyl)-2-formylcymantrene (AFCMT) has been resolved into enantiomers through an intermediate formation of diastereomeric complexes with (S)-Ala-(S)-Ala, (S)-Ala-Gly and Gly-(S)-Ala.By the X-ray anomalous dispersion method the absolute configuration of its enantiomers has been determined: (-)436 AFCMT-(S), (+)436 AFCMT-(R).Alkylation of enantiomeric complexes (R) and (S)-AFCMT-(GlyGly) Cu(II) with acetaldehyde gives, respectively, (R)- and (S)-Thr with an asymmetric yield of 92-98percent and (R)- and (S)-allo-Thr with an asymmetric yield of 95-100percent, only the N-terminal glycine being alkylated.The AFCMT enantiomers were also employed for retroracemisation of (R,S)-Ala-(R,S)-Nva; in this case an excess of (S)-Ala and (R)-Nva is obtained for (S)-AFCMT. (R)- and (S)-AFCMT are not liable to racemisation in the course of the threonine synthesis and retroracemisation of dipeptides and can be repeatedly employed for these transformations.
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