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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 demonstrated effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong hydrogen bond between the amide linker and the chloride on silicon in the transition state contributes to the high reactivity of the catalyst 3a.

SUBMITTER: Qu B

PROVIDER: S-EPMC7853668 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Rational Design of New Dihydrobenzooxophosphole-Based Lewis Base Organocatalysts.

Qu Bo B Samankumara Lalith P LP Saha Anjan A Schumer Mac G MG Han Zhengxu S ZS Haddad Nizar N Busacca Carl A CA Yee Nathan K NK Kozlowski Marisa C MC Song Jinghua J JJ Senanayake Chris H CH

Synlett : accounts and rapid communications in synthetic organic chemistry 20200401 6

A series of new dihydrobenzooxophosphole-based Lewis Base organocatalysts were designed and synthesized. They are demonstrated effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong hydrogen bond between the amide linker and the chloride on silicon in the transition state contributes to the high reactivity of the catalyst <b>3a</b>. ...[more]

PMID: 33542591

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