Non-bonding 1,5-S⋯O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles-Reference-Cited by-同舟云学术

Non-bonding 1,5-S⋯O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles

Published:2016 Issue:12 Volume:7 Page:6919-6927
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Robinson Emily R. T.¹²³⁴⁵,Walden Daniel M.⁶⁷⁸⁹,Fallan Charlene¹²³⁴⁵,Greenhalgh Mark D.¹²³⁴⁵,Cheong Paul Ha-Yeon⁶⁷⁸⁹,Smith Andrew D.¹²³⁴⁵

Affiliation:

1. EaStCHEM

2. School of Chemistry

3. University of St Andrews

4. North Haugh

5. UK

6. Department of Chemistry

7. Oregon State University

8. Corvallis

9. USA

Abstract

Isothiourea-catalyzed annulations of 2-acyl benzazoles and α,β-unsaturated acyl ammoniums are tuned to form lactams or lactones (up to 99% ee). Computations highlight the governing roles of S⋯O and CH⋯O interactions.

Funder

National Science Foundation

European Research Council

Engineering and Physical Sciences Research Council

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/SC/C6SC00940A

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