Rational Design of New Dihydrobenzooxophosphole-Based Lewis Base Organocatalysts

Abstract A series of new dihydrobenzooxophosphole-based Lewis base organocatalysts were designed and synthesized. They are shown to be effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong hydrogen bonds between the amide lin...

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2020-04, Vol.31 (6), p.587-591
Main Authors: Qu, Bo, Samankumara, Lalith P., Saha, Anjan, Schumer, Mac G., Han, Zhengxu S., Haddad, Nizar, Busacca, Carl A., Yee, Nathan K., Kozlowski, Marisa C., Song, Jinghua J., Senanayake, Chris H.
Format: Article
Language:English
Subjects:
cluster
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract A series of new dihydrobenzooxophosphole-based Lewis base organocatalysts were designed and synthesized. They are shown to be effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong hydrogen bonds between the amide linker and the chloride on silicon in the transition state contribute to the high reactivity of the catalyst.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0039-1690851