Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

Kaushalendra Patel; Veeranjaneyulu Lanke; Ilan Marek

doi:https://doi.org/10.1021/jacs.2c01695

Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

Kaushalendra Patel, Veeranjaneyulu Lanke, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

Abstract

Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.

Original language	English
Pages (from-to)	7066-7071
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	144
Issue number	16
DOIs	https://doi.org/10.1021/jacs.2c01695
State	Published - 27 Apr 2022

Keywords

Carbon
Catalysis
Molecular Structure
Stereoisomerism

Access to Document

https://doi.org/10.1021/jacs.2c01695

Cite this

@article{6ecd9525728b48e9b47de99da2eff951,

title = "Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters",

abstract = "Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.",

keywords = "Carbon, Catalysis, Molecular Structure, Stereoisomerism",

author = "Kaushalendra Patel and Veeranjaneyulu Lanke and Ilan Marek",

note = "Publisher Copyright: {\textcopyright}",

year = "2022",

month = apr,

day = "27",

doi = "https://doi.org/10.1021/jacs.2c01695",

language = "الإنجليزيّة",

volume = "144",

pages = "7066--7071",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

AU - Patel, Kaushalendra

AU - Lanke, Veeranjaneyulu

AU - Marek, Ilan

N1 - Publisher Copyright: ©

PY - 2022/4/27

Y1 - 2022/4/27

N2 - Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.

AB - Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.

KW - Carbon

KW - Catalysis

KW - Molecular Structure

KW - Stereoisomerism

UR - http://www.scopus.com/inward/record.url?scp=85128685976&partnerID=8YFLogxK

U2 - https://doi.org/10.1021/jacs.2c01695

DO - https://doi.org/10.1021/jacs.2c01695

M3 - مقالة

C2 - 35412821

SN - 0002-7863

VL - 144

SP - 7066

EP - 7071

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 16

ER -

Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this