Published June 19, 2002
| Supplemental Material
Journal Article
Open
The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes
- Creators
- Northrup, Alan B.
- MacMillan, David W. C.
Chicago
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Abstract
The first enantioselective catalytic direct cross-aldol reaction that employs nonequivalent aldehydes has been accomplished using proline as the reaction catalyst. Structural variation in both the aldol donor (R_1 = Me, n-Bu, Bn, 91 to >99%) and aldol acceptor (R_2 = I-Pr, I-Bu, c-C6H11, Et, Ph, 97−99% ee) are possible while maintaining high reaction efficiency (75−88% yield). Significantly, this new aldol variant allows facile enantioselective access to a broad range of β-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.
Additional Information
© 2002 American Chemical Society. Received March 19, 2002. Publication Date (Web): May 8, 2002. We thank S. P. Brown, N. C. Goodwin, and I. K. Mangion for early contributions to this work. Financial support was provided by AstraZeneca, GlaxoSmithKline, Johnson and Johnson, Lilly, Merck Research Laboratories, and Pfizer. A.B.N. is grateful for an NSF predoctoral fellowship.Attached Files
Supplemental Material - ja0262378_s.pdf
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Additional details
- Eprint ID
- 76965
- DOI
- 10.1021/ja0262378
- Resolver ID
- CaltechAUTHORS:20170426-154358045
- AstraZeneca
- GlaxoSmithKlin
- Johnson and Johnson
- Lilly
- Merck Research Laboratories
- Pfizer
- NSF Predoctoral Fellowship
- Created
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2017-04-26Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field