Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

Kaiheng Zhang; Marta Meazza; Anabel Izaga; Clotilde Contamine; M. Concepción Gimeno; Raquel P. Herrera; Ramon Rios

doi:10.1055/s-0036-1588347

Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

Kaiheng Zhang
, Marta Meazza
, Anabel Izaga
, Clotilde Contamine
, M. Concepción Gimeno
, Raquel P. Herrera
, Ramon Rios

Chemistry

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

22 Scopus citations

Abstract

We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.

Original language	British English
Article number	ss-2016-z0674-op
Pages (from-to)	167-174
Number of pages	8
Journal	Synthesis
Volume	49
Issue number	1
DOIs	https://doi.org/10.1055/s-0036-1588347
State	Published - 3 Jan 2017

Keywords

asymmetric synthesis
cycloaddition
cyclopentanes
organocatalysis
synergistic catalysis

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10.1055/s-0036-1588347

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title = "Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers",

abstract = "We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.",

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author = "Kaiheng Zhang and Marta Meazza and Anabel Izaga and Clotilde Contamine and Gimeno, \{M. Concepci{\'o}n\} and Herrera, \{Raquel P.\} and Ramon Rios",

note = "Funding Information: K.Z., M.M., C.C. and R.R. are grateful for EPSRC Core Capability Funding (EP/K039466/1). C.C. thanks the ERASMUS program for financial support. A.I., M.C.G. and R.P.H. thank the Ministerio de Economia y Competitividad (MINECO/FEDER CTQ2016-75816-C2-1-P), the Spanish High Research Council (CSIC) (PIE-201580I010) and Gobierno de Aragon-Fondo Social Europeo (E77 and E104) for financial support. Publisher Copyright: {\textcopyright} 2017 Georg Thieme Verlag Stuttgart, New York.",

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T1 - Synergistic Catalysis

T2 - Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

AU - Zhang, Kaiheng

AU - Meazza, Marta

AU - Izaga, Anabel

AU - Contamine, Clotilde

AU - Gimeno, M. Concepción

AU - Herrera, Raquel P.

AU - Rios, Ramon

N1 - Funding Information: K.Z., M.M., C.C. and R.R. are grateful for EPSRC Core Capability Funding (EP/K039466/1). C.C. thanks the ERASMUS program for financial support. A.I., M.C.G. and R.P.H. thank the Ministerio de Economia y Competitividad (MINECO/FEDER CTQ2016-75816-C2-1-P), the Spanish High Research Council (CSIC) (PIE-201580I010) and Gobierno de Aragon-Fondo Social Europeo (E77 and E104) for financial support. Publisher Copyright: © 2017 Georg Thieme Verlag Stuttgart, New York.

PY - 2017/1/3

Y1 - 2017/1/3

N2 - We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.

AB - We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.

KW - asymmetric synthesis

KW - cycloaddition

KW - cyclopentanes

KW - organocatalysis

KW - synergistic catalysis

UR - https://www.scopus.com/pages/publications/85000956547

U2 - 10.1055/s-0036-1588347

DO - 10.1055/s-0036-1588347

M3 - Article

AN - SCOPUS:85000956547

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VL - 49

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JO - Synthesis

JF - Synthesis

IS - 1

M1 - ss-2016-z0674-op

ER -

Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

Abstract

Keywords

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