41418-00-2Relevant academic research and scientific papers
Chiral auxiliary based reductive alkylation of α, α-diallkyl β-phosphonyl esters
Bau, Jr-Sheng,Chen, I-Chia,Yang, Zhen-Xing,Zhu, Jia-Liang
, p. 531 - 541 (2013/07/27)
Acyclic α, α-disubstituted β-phosphonyl esters containing chiral alcoholic auxiliaries were efficiently prepared and evaluated for the lithium naphthalenide-mediated asymmetric reductive alkylation. Among which, the best diastereoselectivity was received fromthe substrates bearing a (-)-phenylmenthyl group in leading to alkylated esters with up to 83:17 dr. The diastereoselectivity is proven to be controlled by the π-facial differentiation created by the chiral ester as well as the geometry of tetrasubstituted enolates generated by the reductive cleavage of C-P bond.
