由 L-脯氨酸和 L-丝氨酸衍生的β-酮膦酸酯还原合成 syn-γ-氨基-β-羟基膦酸酯。
Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine.
机构信息
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Mor., México.
出版信息
Molecules. 2010 Mar 4;15(3):1291-301. doi: 10.3390/molecules15031291.
Abstract
The reduction of gamma-N-benzylamino-beta-ketophosphonates 6 and 10, readily available from L-proline and L-serine, respectively, can be carried out in high diastereoselectivity with catecholborane (CB) in THF at -78 degrees C to produce the syn-gamma-N-benzylamino-beta-hydroxyphosphonates 11 and 13 as a single detectable diastereoisomer, under non-chelation or Felkin-Anh model control.
摘要
γ-N-苄基氨基-β-酮膦酸酯 6 和 10 可分别由 L-脯氨酸和 L-丝氨酸制备得到，在非螯合或费尔金-安恩模型控制下，用邻苯二酚硼烷（CB）在四氢呋喃（THF）中于-78°C 进行还原，可以高非对映选择性地得到单一可检测的非对映异构体的顺式-γ-N-苄基氨基-β-羟基膦酸酯 11 和 13。
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