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ChemInform Abstract: Studies in Polypropionate Synthesis: High π-Face Selectivity in syn and anti Aldol Reactions of Chiral Boron Enolates of Lactate-Derived Ketones.

✍ Scribed by I. PATERSON; D. J. WALLACE; S. M. VELAZQUEZ

Book ID
112021347
Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
26
Category
Article
ISSN
0931-7597

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Aldol reactions in polypropionate synthe
Aldol reactions in polypropionate synthesis: High π-face selectivity of enol borinates from α-chiral methyl and ethyl ketones under substrate control
✍ Ian Paterson; Jonathan M. Goodman; Masahiko Isaka 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 277 KB

Use of (c-CgH11)2BCl in the anti-selective aldol reaction of the u-chiral ethylketone 2 leads to high stercoselectivity (>94%) for the 1,2-anti-2,4-anti isomer 7. The related u-chiral methylketone aldol reaction, 8 --t 9, proceeds with 84-93% diastereoselectivity for a range of boron reagents.