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
- Abstract:
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(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...
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- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Version of record, pdf, 563.1KB)
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- Publisher copy:
- 10.3762/bjoc.15.116
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Authors
Bibliographic Details
- 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:
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1860-5397
- Source identifiers:
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1014223
Item Description
- Keywords:
- Pubs id:
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pubs:1014223
- UUID:
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uuid:6ac7b66c-96fb-4ff9-a3c4-42a30e79d456
- Local pid:
- pubs:1014223
- Deposit date:
- 2019-06-21
Terms of use
- 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.
- Licence:
- CC Attribution (CC BY)
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