Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation-Intramolecular Cyclization-Silicon Activation

Maya Preshel-Zlatsin; Fa-Guang Zhang; Guillaume Eppe; Ilan Marek

doi:10.1055/s-0035-1561666

Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation-Intramolecular Cyclization-Silicon Activation

Maya Preshel-Zlatsin, Fa-Guang Zhang, Guillaume Eppe, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The diastereoselective carbometalation reaction of cyclopropenyl esters followed by reaction with acylsilanes provides γ-silylated lactones that undergo a 'sila-Grob' fragmentation to give pyrone enolates as a new source of acyclic δ-diketones, δ-keto acid, and δ-keto ester derivatives possessing a quaternary stereocenter.

Original language	English
Article number	ss-2016-c0205-op
Pages (from-to)	3279-3286
Number of pages	8
Journal	Synthesis
Volume	48
Issue number	19
DOIs	https://doi.org/10.1055/s-0035-1561666
State	Published - 4 Oct 2016

Keywords

carbometalation
cyclopropenes
fragmentation
quaternary carbon stereocenters
silicon activation

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1055/s-0035-1561666

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title = "Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation-Intramolecular Cyclization-Silicon Activation",

abstract = "The diastereoselective carbometalation reaction of cyclopropenyl esters followed by reaction with acylsilanes provides γ-silylated lactones that undergo a 'sila-Grob' fragmentation to give pyrone enolates as a new source of acyclic δ-diketones, δ-keto acid, and δ-keto ester derivatives possessing a quaternary stereocenter.",

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author = "Maya Preshel-Zlatsin and Fa-Guang Zhang and Guillaume Eppe and Ilan Marek",

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year = "2016",

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doi = "10.1055/s-0035-1561666",

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T1 - Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation-Intramolecular Cyclization-Silicon Activation

AU - Preshel-Zlatsin, Maya

AU - Zhang, Fa-Guang

AU - Eppe, Guillaume

AU - Marek, Ilan

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2016/10/4

Y1 - 2016/10/4

N2 - The diastereoselective carbometalation reaction of cyclopropenyl esters followed by reaction with acylsilanes provides γ-silylated lactones that undergo a 'sila-Grob' fragmentation to give pyrone enolates as a new source of acyclic δ-diketones, δ-keto acid, and δ-keto ester derivatives possessing a quaternary stereocenter.

AB - The diastereoselective carbometalation reaction of cyclopropenyl esters followed by reaction with acylsilanes provides γ-silylated lactones that undergo a 'sila-Grob' fragmentation to give pyrone enolates as a new source of acyclic δ-diketones, δ-keto acid, and δ-keto ester derivatives possessing a quaternary stereocenter.

KW - carbometalation

KW - cyclopropenes

KW - fragmentation

KW - quaternary carbon stereocenters

KW - silicon activation

UR - http://www.scopus.com/inward/record.url?scp=84974668012&partnerID=8YFLogxK

U2 - 10.1055/s-0035-1561666

DO - 10.1055/s-0035-1561666

M3 - مقالة

SN - 0039-7881

VL - 48

SP - 3279

EP - 3286

JO - Synthesis

JF - Synthesis

IS - 19

M1 - ss-2016-c0205-op

ER -

Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation-Intramolecular Cyclization-Silicon Activation

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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