alpha-Hydroxyphosphonic acid derivatives of 2-azanorbornane: synthesis, DFT calculations, and crystal structure analysis

作者:Olszewski Tomasz K; Wojaczynska Elzbieta*; Wieczorek Robert; Bakowicz Julia
来源:Tetrahedron: Asymmetry , 2015, 26(12-13): 601-607.
DOI:10.1016/j.tetasy.2015.04.012

摘要

Highly diastereoselective hydrophosphonylation of 2-azanorbornane aldehyde exo-1 with silylated phosphorus esters yielded the (S)-alpha-hydroxyphosphonic acid exo-3a. The use of endo-2 gives the isomer with the opposite configuration at the new stereogenic center (R)-endo-4a. X-ray analysis revealed that exo-3a crystallizes in the orthorhombic space group P2(1)2(1)2(1) with two crystallographically independent molecules, one zwitterionic and the other forming a salt with HBr.

  • 出版日期2015-7-15