| Synthesis, circular dichroism, and absolute stereochemistry of a Fecht acid analog and related compounds | |
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MedLine Citation:
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PMID: 10857059 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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2,6-Dimethylspiro[3.3]heptane-2,6-dicarboxylic acid (2), an analog of the Fecht acid (1), was enantioresolved by the method of (1S,2R,4R)-(-)-2,10-camphorsultam yielding enantiopure acid (+)-2, the S absolute configuration of which was unambiguously determined by X-ray crystallography of camphorsultam amide derivative (R)-(-)-12b and chemical correlation. To determine the absolute configuration of chiral spiro[3.3]heptane compounds by the circular dichroism (CD) exciton chirality method, acid (+)-2 was converted to (+)-2,6-bis(phenylacetylenyl)-2,6-dimethylspiro[3.3]heptane (3) and (+)-2,6-bis(4-methoxyphenylacetylenyl)-2,6-dimethylspiro[3.3]heptane (4). The CD spectra of (+)-3 and (+)-4 exhibit intense exciton split Cotton effects of positive chirality, from which their S absolute configurations were confirmed. |
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Authors:
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Murai; Soutome; Yoshida; Osawa; Harada |
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Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: Enantiomer Volume: 5 ISSN: 1024-2430 ISO Abbreviation: Enantiomer Publication Date: 2000 |
Date Detail:
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Created Date: 2000-06-16 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9612491 Medline TA: Enantiomer Country: ENGLAND |
Other Details:
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Languages: Eng Pagination: 197-202 Citation Subset: - |
Affiliation:
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Institute for Chemical Reaction Science, Tohoku University, Sendai, Japan. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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