Diastereodivergent carbometalation/oxidation/selective ring opening: Formation of all-carbon quaternary stereogenic centers in acyclic systems

Pierre Olivier Delaye; Dorian Didier; Ilan Marek

doi:10.1002/anie.201300664

Diastereodivergent carbometalation/oxidation/selective ring opening: Formation of all-carbon quaternary stereogenic centers in acyclic systems

Pierre Olivier Delaye, Dorian Didier, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

A twofer: The title reaction sequence for cyclopropenes allows the preparation of aldehydes bearing α-quaternary stereocenters in a one pot-reaction from readily available starting materials. Through a diastereodivergent carbometalation reaction, both enantiomers of the corresponding aldehyde were obtained from the same cyclopropene derivative (see scheme).

Original language	English
Pages (from-to)	5333-5337
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	20
DOIs	https://doi.org/10.1002/anie.201300664
State	Published - 10 May 2013

Keywords

cleavage reactions
copper
metalation
oxidation
synthetic methods

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Access to Document

10.1002/anie.201300664

Cite this

@article{63c9e2ea753c4507a3723f5f33c098ab,

title = "Diastereodivergent carbometalation/oxidation/selective ring opening: Formation of all-carbon quaternary stereogenic centers in acyclic systems",

abstract = "A twofer: The title reaction sequence for cyclopropenes allows the preparation of aldehydes bearing α-quaternary stereocenters in a one pot-reaction from readily available starting materials. Through a diastereodivergent carbometalation reaction, both enantiomers of the corresponding aldehyde were obtained from the same cyclopropene derivative (see scheme).",

keywords = "cleavage reactions, copper, metalation, oxidation, synthetic methods",

author = "Delaye, \{Pierre Olivier\} and Dorian Didier and Ilan Marek",

year = "2013",

month = may,

day = "10",

doi = "10.1002/anie.201300664",

language = "الإنجليزيّة",

volume = "52",

pages = "5333--5337",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "20",

}

TY - JOUR

T1 - Diastereodivergent carbometalation/oxidation/selective ring opening

T2 - Formation of all-carbon quaternary stereogenic centers in acyclic systems

AU - Delaye, Pierre Olivier

AU - Didier, Dorian

AU - Marek, Ilan

PY - 2013/5/10

Y1 - 2013/5/10

N2 - A twofer: The title reaction sequence for cyclopropenes allows the preparation of aldehydes bearing α-quaternary stereocenters in a one pot-reaction from readily available starting materials. Through a diastereodivergent carbometalation reaction, both enantiomers of the corresponding aldehyde were obtained from the same cyclopropene derivative (see scheme).

AB - A twofer: The title reaction sequence for cyclopropenes allows the preparation of aldehydes bearing α-quaternary stereocenters in a one pot-reaction from readily available starting materials. Through a diastereodivergent carbometalation reaction, both enantiomers of the corresponding aldehyde were obtained from the same cyclopropene derivative (see scheme).

KW - cleavage reactions

KW - copper

KW - metalation

KW - oxidation

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84877298211&partnerID=8YFLogxK

U2 - 10.1002/anie.201300664

DO - 10.1002/anie.201300664

M3 - مقالة

SN - 1433-7851

VL - 52

SP - 5333

EP - 5337

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 20

ER -

Diastereodivergent carbometalation/oxidation/selective ring opening: Formation of all-carbon quaternary stereogenic centers in acyclic systems

Abstract

Keywords

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this