Diastereo‐ and Enantioselective Hydrophosphination of Cyclopropenes under Lanthanocene Catalysis

The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo‐ and enantioselective hydrophosphination of 3,3‐disubstituted cyclopropenes...

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Published inAngewandte Chemie International Edition Vol. 62; no. 34; pp. e202308488 - n/a
Main Authors Lin, Xiaobin, An, Kun, Zhuo, Qingde, Nishiura, Masayoshi, Cong, Xuefeng, Hou, Zhaomin
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 21.08.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Atom economy
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cyclopropenes
Enantiomers
Enantioselective
Hydrophosphination
Lanthanocene Catalyst
Organic compounds
Phosphine
Phosphines
Physical Sciences
Route selection
Science & Technology
Substrates
Hydrophosphination
Cyclopropenes
HYDROBORATION
ACTIVATION
Phosphine
COMPLEXES
HYDROSILYLATION
STRUCTURAL-CHARACTERIZATION
POLYMERIZATION
CHIRAL CYCLOPENTADIENYL LIGANDS
CARBOMETALATION
DESYMMETRIZATION
Lanthanocene Catalyst
H BOND ADDITION
Enantioselective
phosphine
hydrophosphination
lanthanocene catalyst
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Abstract The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo‐ and enantioselective hydrophosphination of 3,3‐disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C2‐symmetric 5,6‐dioxy‐4,7‐trans‐dialkyl‐substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo‐ and enantioselectivity, broad substrate scope, and no need for a directing group. A chiral lanthanocene complex served as a unique catalyst for the asymmetric hydrophosphination of cyclopropenes with phosphines, efficiently affording a new family of chiral phosphinocyclopropane derivatives in high yields with good diastereo‐ and enantioselectivity and without the need for a directing group.
AbstractList The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo‐ and enantioselective hydrophosphination of 3,3‐disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C 2 ‐symmetric 5,6‐dioxy‐4,7‐ trans ‐dialkyl‐substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo‐ and enantioselectivity, broad substrate scope, and no need for a directing group.
The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo- and enantioselective hydrophosphination of 3,3-disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C-2-symmetric 5,6-dioxy-4,7-trans-dialkyl-substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo- and enantioselectivity, broad substrate scope, and no need for a directing group.
The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo- and enantioselective hydrophosphination of 3,3-disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C2-symmetric 5,6-dioxy-4,7-trans-dialkyl-substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100% atom efficiency, good diastereo- and enantioselectivity, broad substrate scope, and no need for a directing group.
The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo- and enantioselective hydrophosphination of 3,3-disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C2 -symmetric 5,6-dioxy-4,7-trans-dialkyl-substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo- and enantioselectivity, broad substrate scope, and no need for a directing group.The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo- and enantioselective hydrophosphination of 3,3-disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C2 -symmetric 5,6-dioxy-4,7-trans-dialkyl-substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo- and enantioselectivity, broad substrate scope, and no need for a directing group.
The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo‐ and enantioselective hydrophosphination of 3,3‐disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C2‐symmetric 5,6‐dioxy‐4,7‐trans‐dialkyl‐substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo‐ and enantioselectivity, broad substrate scope, and no need for a directing group. A chiral lanthanocene complex served as a unique catalyst for the asymmetric hydrophosphination of cyclopropenes with phosphines, efficiently affording a new family of chiral phosphinocyclopropane derivatives in high yields with good diastereo‐ and enantioselectivity and without the need for a directing group.
Author Hou, Zhaomin
Cong, Xuefeng
Nishiura, Masayoshi
An, Kun
Zhuo, Qingde
Lin, Xiaobin
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Issue 34
Keywords Hydrophosphination
Cyclopropenes
HYDROBORATION
ACTIVATION
Phosphine
COMPLEXES
HYDROSILYLATION
STRUCTURAL-CHARACTERIZATION
POLYMERIZATION
CHIRAL CYCLOPENTADIENYL LIGANDS
CARBOMETALATION
DESYMMETRIZATION
Lanthanocene Catalyst
H BOND ADDITION
Enantioselective
phosphine
hydrophosphination
lanthanocene catalyst
Language English
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Snippet The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably...
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SubjectTerms Atom economy
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cyclopropenes
Enantiomers
Enantioselective
Hydrophosphination
Lanthanocene Catalyst
Organic compounds
Phosphine
Phosphines
Physical Sciences
Route selection
Science & Technology
Substrates
Title Diastereo‐ and Enantioselective Hydrophosphination of Cyclopropenes under Lanthanocene Catalysis
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202308488
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001089013400001
https://www.ncbi.nlm.nih.gov/pubmed/37405669
https://www.proquest.com/docview/2851804627
https://www.proquest.com/docview/2833645801
Volume 62
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