Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides

Marta Meazza; Maria Ashe; Hun Yi Shin; Hye Sung Yang; Andrea Mazzanti; Jung Woon Yang; Ramon Rios

doi:10.1021/acs.joc.5b02801

Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides

Marta Meazza
, Maria Ashe
, Hun Yi Shin
, Hye Sung Yang
, Andrea Mazzanti
, Jung Woon Yang
, Ramon Rios

Chemistry

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

29 Scopus citations

Abstract

Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.

Original language	British English
Pages (from-to)	3488-3500
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	81
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.5b02801
State	Published - 6 May 2016

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title = "Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides",

abstract = "Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.",

author = "Marta Meazza and Maria Ashe and Shin, \{Hun Yi\} and Yang, \{Hye Sung\} and Andrea Mazzanti and Yang, \{Jung Woon\} and Ramon Rios",

note = "Funding Information: M.A., M.M., and R.R. acknowledge the European Regional Development Fund (ERDF) for cofinancing the AI-CHEMChem project (No. 4061) through the INTERREG IV A France (Channel)?England cross-border cooperation Programme. M.A., M.M., and R.R. are grateful for the EPSRC Core Capability Funding (EP/K039466/1). J.W.Y. thanks the NRF Nano Material Technology Development Program (2012M3A7B4049652) for financial support. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.joc.5b02801",

language = "British English",

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T1 - Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides

AU - Meazza, Marta

AU - Ashe, Maria

AU - Shin, Hun Yi

AU - Yang, Hye Sung

AU - Mazzanti, Andrea

AU - Yang, Jung Woon

AU - Rios, Ramon

N1 - Funding Information: M.A., M.M., and R.R. acknowledge the European Regional Development Fund (ERDF) for cofinancing the AI-CHEMChem project (No. 4061) through the INTERREG IV A France (Channel)?England cross-border cooperation Programme. M.A., M.M., and R.R. are grateful for the EPSRC Core Capability Funding (EP/K039466/1). J.W.Y. thanks the NRF Nano Material Technology Development Program (2012M3A7B4049652) for financial support. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/5/6

Y1 - 2016/5/6

N2 - Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.

AB - Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.

UR - https://www.scopus.com/pages/publications/84968719151

U2 - 10.1021/acs.joc.5b02801

DO - 10.1021/acs.joc.5b02801

M3 - Article

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SN - 0022-3263

VL - 81

SP - 3488

EP - 3500

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides

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