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Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid.

Abstract:

The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-[small alpha]-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and trans-(3R,4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four ste...

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Publication status:
Published

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Publisher copy:
10.1039/b407558g

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
2
Issue:
19
Pages:
2763-2776
Publication date:
2004-10-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:dc404f43-a889-46d7-b19d-1e9895ef9554
Source identifiers:
110544
Local pid:
pubs:110544

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