Stereoselective Preparation of Distant Stereocenters (1,5) within Acyclic Molecules

Anthony Cohen; Jean Chagneau; Ilan Marek

doi:10.1021/acscatal.0c01762

Stereoselective Preparation of Distant Stereocenters (1,5) within Acyclic Molecules

Anthony Cohen, Jean Chagneau, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The development of a modular and diastereodivergent approach to acyclic products bearing two distant stereocenters in a 1,5 relationship is reported. Remarkably, it was accomplished in just three catalytic steps from commercially available alkynes. This sequence generates the desired distant stereocenters efficiently and with high diastereocontrol and a perfect E:Z ratio. The approach was used for a noniterative formal synthesis of the α-tocopherol side chain.

Original language	English
Pages (from-to)	7154-7161
Number of pages	8
Journal	ACS Catalysis
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/acscatal.0c01762
State	Published - 2 Jul 2020

Keywords

alkenyl cyclopropane
cyclopropenes
distant stereocenters
ring-opening
tocopherol

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

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10.1021/acscatal.0c01762

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title = "Stereoselective Preparation of Distant Stereocenters (1,5) within Acyclic Molecules",

abstract = "The development of a modular and diastereodivergent approach to acyclic products bearing two distant stereocenters in a 1,5 relationship is reported. Remarkably, it was accomplished in just three catalytic steps from commercially available alkynes. This sequence generates the desired distant stereocenters efficiently and with high diastereocontrol and a perfect E:Z ratio. The approach was used for a noniterative formal synthesis of the α-tocopherol side chain. ",

keywords = "alkenyl cyclopropane, cyclopropenes, distant stereocenters, ring-opening, tocopherol",

author = "Anthony Cohen and Jean Chagneau and Ilan Marek",

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year = "2020",

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doi = "10.1021/acscatal.0c01762",

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AU - Chagneau, Jean

AU - Marek, Ilan

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Y1 - 2020/7/2

N2 - The development of a modular and diastereodivergent approach to acyclic products bearing two distant stereocenters in a 1,5 relationship is reported. Remarkably, it was accomplished in just three catalytic steps from commercially available alkynes. This sequence generates the desired distant stereocenters efficiently and with high diastereocontrol and a perfect E:Z ratio. The approach was used for a noniterative formal synthesis of the α-tocopherol side chain.

AB - The development of a modular and diastereodivergent approach to acyclic products bearing two distant stereocenters in a 1,5 relationship is reported. Remarkably, it was accomplished in just three catalytic steps from commercially available alkynes. This sequence generates the desired distant stereocenters efficiently and with high diastereocontrol and a perfect E:Z ratio. The approach was used for a noniterative formal synthesis of the α-tocopherol side chain.

KW - alkenyl cyclopropane

KW - cyclopropenes

KW - distant stereocenters

KW - ring-opening

KW - tocopherol

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U2 - 10.1021/acscatal.0c01762

DO - 10.1021/acscatal.0c01762

M3 - مقالة

SN - 2155-5435

VL - 10

SP - 7154

EP - 7161

JO - ACS Catalysis

JF - ACS Catalysis

IS - 13

ER -

Stereoselective Preparation of Distant Stereocenters (1,5) within Acyclic Molecules

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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