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Citation
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HERO ID
6853821
Reference Type
Journal Article
Title
An efficient asymmetric synthesis of 2-substituted ferrocenecarboxaldehydes
Author(s)
Riant, O; Riant, O; Samuel, O; Samuel, O; Flessner, T; Flessner, T; Taudien, S; Taudien, S; Kagan, HB; Kagan, HB
Year
1997
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Volume
62
Issue
20
Page Numbers
6733-6745
DOI
10.1021/jo970075u
Web of Science Id
WOS:A1997XZ71900012
Abstract
Ferrocenecarboxaldehyde is readily transformed into the acetal of (S)-1,2,4-butanetriol (1,3-dioxane structure) and further methylated to give acetal 15. This can then be ortho-lithiated using t-BuLi with very high diastereoselectivity (98% de). Electrophilic quenching provided a large array of compounds of established stereochemistry. Controlled hydrolysis leads to many ortho-substituted ferrocenecarboxaldehydes (98% ee) which themselves are starting materials in the synthesis of various classes of enantiopure ferrocene derivatives with planar chirality of predictable absolute configuration.<
Tags
OPPT REs
•
OPPT_1,4-Dioxane_D. Exposure
Total – title/abstract screening
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