Fields, A.M. and Jones, S. orcid.org/0000-0001-8043-7998 (2019) Synergistic substrate and catalyst effects in the addition of trimethylsilyl cyanide to imines derived from lactic acid. Tetrahedron, 75 (25). pp. 3413-3420. ISSN 0040-4020
Abstract
Trimethylsilylcyanide was added to various imines derived from (2S)-ethyl lactate in the presence of Lewis acids to provide both syn- and anti- β-hydroxy-α-aminonitrile stereoisomers. Syn-products were found to be the major in most instances, however, anti-products were formed in good yield and selectivity in the presence of ZnI 2 & BF 3 ·OEt 2 and N-(−)-α-methylbenzyl substituents via double stereo differentiation.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © 2019 Elsevier Ltd. This is an author produced version of a paper subsequently published in Tetrahedron. Uploaded in accordance with the publisher's self-archiving policy. Article available under the terms of the CC-BY-NC-ND licence (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
Keywords: | Lactimine; Strecker reaction; Trimethylsilyl cyanide |
Dates: |
|
Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 22 May 2019 13:00 |
Last Modified: | 03 Dec 2021 10:42 |
Status: | Published |
Publisher: | Elsevier |
Refereed: | Yes |
Identification Number: | 10.1016/j.tet.2019.04.067 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:146387 |