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.
Final published version, 2.95 MBLicence: CC BY

CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard
ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
European Commission
1/10/11 → 30/06/17
Project: Standard

data underpinning "6-exo-trig Michael Addition-Lactonizations for Catalytic Enantioselective Chromenone Synthesis"
Smith, A. D. (Creator), N P, R. M. (Owner), Cordes, D. B. (Owner) & Slawin, A. M. Z. (Owner), University of St Andrews, 30 Nov 2016
DOI: 10.17630/1c5c3fb2-77e3-4830-a2a4-6c76ccee4f21
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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",

year = "2017",

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doi = "10.1039/C6CC10178J",

language = "English",

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T1 - 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

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.

U2 - 10.1039/C6CC10178J

DO - 10.1039/C6CC10178J

M3 - Article

SN - 1359-7345

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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Projects

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

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

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

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