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Prolinol as a Chiral Auxiliary in Organophosphorus Chemistry
Author(s) -
Kozioł Anna E.,
Włodarczyk Adam
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100196
Subject(s) - chemistry , boranes , imine , chirality (physics) , phosphine , borane , asymmetric hydrogenation , enantioselective synthesis , catalysis , alkyl , bicyclic molecule , organocatalysis , combinatorial chemistry , organic chemistry , transition state , axial chirality , stereochemistry , computational chemistry , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , boron
Several strategies for the development of the synthesis of P‐chiral organophosphorus compounds with (L)‐prolinol as a source of chirality have been examined. A reaction of L ‐prolinol with a set of different alkyl/arylphosphonous acid diamides led in most of the cases to the quantitative formation of the appropriate bicyclic oxazaphospholidines with complete diastereo and enantioselectivity. The latter were reacted with BH 3 complex and the formed borane analogues were submitted to structural modifications leading to tertiary phosphine‐boranes. Additionally, the effectiveness of oxazaphospholidines as ligands in transition metal asymmetric catalysis has been tested in hydrogenation of dehydroaminoacid esters and imine.