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Studies in macrolide synthesis: aldol condensations of chiral ethylketones via boron enolates.

โœ Scribed by Ian Paterson; Cynthia K McClure

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
341 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A/do/ condensation of chiraal ethylketones 8 and 9,via their 9-BBN or "BupB eno/ates,with methacrolein and acetaldehyde gives mainly the &&&I adduct, 8 -+ 14 or 9 + 18. The chiral reagent (+)-(lpc)~OTf, in the presence of EL& is used to enhance the formation of 14 and 78, while

๐Ÿ“œ SIMILAR VOLUMES

Studies in macrolide synthesis: A stereo
Studies in macrolide synthesis: A stereocontrolled synthesis of a (9S)-macrolide intermediate for oleandomycin using chiral boron reagents.
โœ Ian Paterson; M.Anne Lister; Roger D. Norcross ๐Ÿ“‚ Article ๐Ÿ“… 1992 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 350 KB

The (9s)-macrolide 1 (P = TBS) was prepared in 14 steps (5% yield) with 63% overall ds starting from the ethyl ketone ($2. The Cl-C7 and Q-C13 segments, 3 and 4, were obtained via boron enolate aldol reactions mediated by (+)-and (-)-(Ipc)zBOTf, respectively. Conventional reduction conditions using

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Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes. Total synthesis of (3S,4S)-Statine
โœ Cesare Gennari; Daniela Moresca; Anna Vulpetti; Gilles Pain ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 930 KB

Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacet