Organic Letters

, том 24 , издание 1 , страницы 110-114

Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane

Тип публикации: Journal Article

Дата публикации: 2021-12-15

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.1c03681

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PubMed ID: 34908426

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

The stereoselective synthesis of bicyclo[1.1.1]pentane (BCP) benzylamine derivatives from [1.1.1]propellane and mesityl sulfinimines via metal hydride hydrogen atom transfer (MH HAT) is reported. Medicinally relevant heterocyclic BCP methanamines are prepared with high diastereoselectivity. The strategic impact of the method is demonstrated via the streamlined synthesis of the BCP analogue of a key levocetirizine intermediate. Mechanistic evidence for a competitive H2 evolution pathway and the importance of controlled silane addition during reaction initiation are disclosed.

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Shelp R. A. et al. Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane // Organic Letters. 2021. Vol. 24. No. 1. pp. 110-114.

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Shelp R. A., Merchant R. R., Hughes J. M. E., Walsh P. J. Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane // Organic Letters. 2021. Vol. 24. No. 1. pp. 110-114.

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TY - JOUR

DO - 10.1021/acs.orglett.1c03681

UR - https://doi.org/10.1021/acs.orglett.1c03681

TI - Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane

T2 - Organic Letters

AU - Shelp, Russell A

AU - Merchant, Rohan R

AU - Hughes, Jonathan M E

AU - Walsh, Patrick J

PY - 2021

DA - 2021/12/15

PB - American Chemical Society (ACS)

SP - 110-114

IS - 1

VL - 24

PMID - 34908426

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2021_Shelp,

author = {Russell A Shelp and Rohan R Merchant and Jonathan M E Hughes and Patrick J Walsh},

title = {Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane},

journal = {Organic Letters},

year = {2021},

volume = {24},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.orglett.1c03681},

number = {1},

pages = {110--114},

doi = {10.1021/acs.orglett.1c03681}

}

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Shelp, Russell A., et al. “Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane.” Organic Letters, vol. 24, no. 1, Dec. 2021, pp. 110-114. https://doi.org/10.1021/acs.orglett.1c03681.