- Abstract:
-
(R,R)-Dimethyl tartrate acetonide 7 in THF/HMPA undergoes deprotonation with LDA and reaction at −78 °C during 12–72 h with a range of alkyl halides, including non-activated substrates, to give single diastereomers (at the acetonide) of monoalkylated tartrates 17, 24, 33a–f, 38a,b, 41 of R,R-configuration, i.e., a stereoretentive process (13–78% yields). Separable trans-dialkylated tartrates 34a–f can be co-produced in small amounts (9–14%) under these conditions, and likely arise from the ac...
Expand abstract - Publication status:
- Published
- Peer review status:
- Peer reviewed
- Version:
- Publisher's Version
- Files:
-
-
(pdf, 563.1kb)
-
- Publisher copy:
- 10.3762/bjoc.15.116
-
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- Publisher:
- Beilstein-Institut Publisher's website
- Journal:
- Beilstein Journal of Organic Chemistry Journal website
- Volume:
- 15
- Pages:
- 1194-1202
- Publication date:
- 2019-05-31
- Acceptance date:
- 2019-05-14
- DOI:
- ISSN:
-
1860-5397
- Pubs id:
-
pubs:1014223
- URN:
-
uri:6ac7b66c-96fb-4ff9-a3c4-42a30e79d456
- UUID:
-
uuid:6ac7b66c-96fb-4ff9-a3c4-42a30e79d456
- Local pid:
- pubs:1014223
- Copyright holder:
- Sintim et al.
- Copyright date:
- 2019
- Notes:
- © 2019 Sintim et al. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
Journal article
Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids
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