Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides-Reference-Cited by-同舟云学术

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

Published:2022-02-15 Issue:5 Volume:87 Page:3042-3065
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Bartolo Nicole D.¹^ORCID,Demkiw Krystyna M.¹^ORCID,Read Jacquelyne A.¹^ORCID,Valentín Elizabeth M.²^ORCID,Yang Yingying¹,Dillon Alexandra M.¹^ORCID,Hu Chunhua T.¹^ORCID,Ward Michael D.¹^ORCID,Woerpel K. A.¹^ORCID

Affiliation:

1. Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States

2. St. Mary’s College of California, 1928 St. Marys Road, Moraga, California 94575, United States

Funder

National Institute of General Medical Sciences

Division of Materials Research

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c02844

Reference110 articles.

1. Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones

2. Torsional strain involving partial bonds. The steric course of the reaction between allyl magnesium bromide and 4-t-butyl-cyclohexanone

3. Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model

4. Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

5. Allylmagnesium Halides Do Not React Chemoselectively Because Reaction Rates Approach the Diffusion Limit

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