结合关环复分解反应对氟化α-氨基酸及其衍生物进行对映选择性合成：分子内π-堆积相互作用作为立体控制的来源。

Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking interactions as a source of stereocontrol.

作者信息

Fustero S, Navarro A, Pina B, Soler J G, Bartolomé A, Asensio A, Simón A, Bravo P, Fronza G, Volonterio A, Zanda M

机构信息

Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain.

出版信息

Org Lett. 2001 Aug 23;3(17):2621-4. doi: 10.1021/ol016087q.

DOI:10.1021/ol016087q

PMID:11506593

Abstract

[reaction: see text]. Hydride reduction of C=N bonds stereocontrolled by intramolecular pi-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta-amino alcohols and alpha-amino acid derivatives, respectively.

摘要

[反应：见正文]。通过1-萘基亚磺酰基与N-芳基的分子内π-堆积相互作用对C=N键进行的氢化物还原、非氧化普默勒重排以及闭环复分解反应，被高效地组合在一起，分别以高度立体选择性的方式合成对映体纯的环状和非环状氟化β-氨基醇以及α-氨基酸衍生物。