Journal article
On the role of p-silyloxy- and p-alkoxyaldehyde protecting groups in Mukaiyama aldol 1,3-diastereocontrol
Tetrahedron letters, Vol.111, 154203
11/23/2022
DOI: 10.1016/j.tetlet.2022.154203
Abstract
Longstanding paradigmatic studies have noted anti-1,3-diastereocontrol in Mukaiyama aldol reactions with p-silyloxy-and p-alkoxyaldehydes. In our efforts to exploit this stereocontrol, we found that an alde-hyde of this type that lacks branching at the 7-carbon led to eroded diastereoselectivity that was restored upon changing the p-protecting group. This suggested the hypothesis that 1,3-anti selectivity in these cases is inversely dependent on the size of the p-protecting group. In testing this hypothesis, Mukaiyama aldol reactions of several analogs of unbranched p-silyloxy-and p-alkoxyaldehydes, varying only the protecting group, showed improved selectivity with smaller silyl and alkyl groups. These results will aid synthetic design as well as provide experimental benchmarks for computational studies.(c) 2022 Elsevier Ltd. All rights reserved.
Details
- Title: Subtitle
- On the role of p-silyloxy- and p-alkoxyaldehyde protecting groups in Mukaiyama aldol 1,3-diastereocontrol
- Creators
- Lucas W. Howell - University of IowaGregory K. Friestad - Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.111, 154203
- Publisher
- Elsevier
- DOI
- 10.1016/j.tetlet.2022.154203
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Number of pages
- 4
- Language
- English
- Date published
- 11/23/2022
- Academic Unit
- Chemistry
- Record Identifier
- 9984353989702771
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