6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

Rifahath Mon N P; David Bradford Cordes; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1039/C6CC10178J

6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

Rifahath Mon N P, David Bradford Cordes, Alexandra Martha Zoya Slawin, Andrew David Smith

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

Abstract

The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.

Original language	English
Pages (from-to)	2555-2558
Journal	Chemical Communications
Volume	53
Issue number	17
Early online date	19 Jan 2017
DOIs	https://doi.org/10.1039/C6CC10178J
Publication status	Published - 28 Feb 2017

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10.1039/C6CC10178JLicence: CC BY

Smith_2017_CC_6-exo_CCBYVoR
Copyright 2017 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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Cite this

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title = "6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis",

abstract = "The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.",

author = "\{N P\}, \{Rifahath Mon\} and Cordes, \{David Bradford\} and Slawin, \{Alexandra Martha Zoya\} and Smith, \{Andrew David\}",

note = "The authors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, RMNP) for funding.The European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged. ADS thanks the Royal Society for a Wolfson Research Merit Award",

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doi = "10.1039/C6CC10178J",

language = "English",

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AU - N P, Rifahath Mon

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The authors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, RMNP) for funding.The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged. ADS thanks the Royal Society for a Wolfson Research Merit Award

PY - 2017/2/28

Y1 - 2017/2/28

N2 - The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.

AB - The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.

UR - https://www.scopus.com/pages/publications/85013929588

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DO - 10.1039/C6CC10178J

M3 - Article

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VL - 53

SP - 2555

EP - 2558

JO - Chemical Communications

JF - Chemical Communications

IS - 17

ER -

6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

Abstract

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CRITICAT CDT: Critical Resource Catalysis - CRITICAT

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis

data underpinning "6-exo-trig Michael Addition-Lactonizations for Catalytic Enantioselective Chromenone Synthesis"

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6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

Abstract

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Other files and links

Fingerprint

Projects

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis

Datasets

data underpinning "6-exo-trig Michael Addition-Lactonizations for Catalytic Enantioselective Chromenone Synthesis"

Cite this