Enantioselective conjugate addition of dialkyl phosphites to nitroalkenes

Recent advances in Michael addition of H-phosphonates

“…For the rst time the enantioselective addition of dialkyl phosphonates to nitroalkenes was successfully carried out in the presence of heterobimetallic (S)-(À)-aluminum lithium bis(binaphthoxide) complex. 69 At the same time, Terada and co-workers developed a highly enantioselective version of 1,4-conjugate addition of diphenyl phosphonate to a broad range of nitroalkenes bearing either aromatic or aliphatic substituents. For this aim they applied axially chiral guanidines as efficient Brønsted base catalyst (Scheme 18).…”

Recent Advances in Metal-Catalyzed C–P Bond Formation

“…In a variation on this theme, addition of dialkyl phosphites to nitroalkenes was catalyzed by an Al-Li-Binol species (ALB) [62]. Coordination of the nitro group to aluminum and activation of the phosphite tautomer by Li binding was proposed to lead to selective P-C bond formation (Scheme 38).…”

Enantioselective Synthesis of β‐Nitrophosphonates Using Immobilized Quinine Organocatalyst on Mesoporous SBA‐15 as an Efficient Recyclable Catalyst

“…It is not surprising that the absolute configuration of the stereogenic α‐or β‐carbon in these phosphonyl compounds strongly influences their biological properties . Although great efforts have been made towards the development of asymmetric approaches for the synthesis of enantiomerically α‐amino phosphonic acids, the synthesis of β‐amino phosphonic acids and their esters are scarcely studied using metal free catalysts,, metal catalyst and organocatalysts under homogeneous system. In this line the asymmetric 1,4 Michael addition of diphenylphosphite to nitroalkenes catalyzed by organocatalyst remains a challenging topic .…”