DIASTEREOSELECTIVITY IN THE ALKYLATION OF CHIRAL 2-AMINOMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDES
- 1 September 1987
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 33 (1) , 1-14
- https://doi.org/10.1080/03086648708074276
Abstract
The alkylation of chiral cyclic diesters of α-aminomethyl-phosphonate derivatives was investigated as a potential route to the asymmetric synthesis of phosphonic acid analogs of α-amino acids. The 1,3,2-dioxaphosphorinanes derived from d,l-2,4-pentanediol (1D-c and 1D-d), which adopt primarily the C-equatorial conformation, were compared to the homologs 1T-c and 1T-e derived from 2-methyl-2,4-pentanediol, in which the aminomethyl moiety is fixed in the axial configuration. While neither series shows high stereoselectivity (de ≤ 50%), it was shown that the two chiral auxiliaries produce asymmetric induction of the opposite sense.Keywords
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