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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:

(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
Version:
Publisher's Version

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Publisher copy:
10.3762/bjoc.15.116

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
Oxford college:
Oriel College
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

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