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Diarylprolinol as an Effective Organocatalyst in Asymmetric Cross‐Aldol Reactions of Two Different Aldehydes.
- Source :
- Chemical Record; Jul2023, Vol. 23 Issue 7, p1-30, 30p
- Publication Year :
- 2023
-
Abstract
- The aldol reaction is one of the most important carbon‐carbon bond‐forming reactions in organic chemistry. Asymmetric direct cross‐aldol reaction of two different aldehydes has been regarded as a difficult reaction because of the side reactions such as self‐aldol reaction and over reaction. We found that trifluoromethyl‐substituted diarylprolinol, α,α‐bis[3,5‐bis(trifluoromethyl)phenyl]‐2‐pyrrolidinemethanol (1), is an effective organocatalyst that promotes several cross‐aldol reactions of aldehydes with excellent diastereo‐ and enantioselectivities. Acetaldehyde can be employed as a suitable nucleophilic aldehyde. Successful electrophilic aldehydes are ethyl glyoxylate, chloroacetaldehyde, dichloroacetaldehyde, chloral, α‐alkyl‐α‐oxo aldehyde, trifluoroacetaldehyde, glyoxal, alkenyl aldehyde, alkynyl aldehyde, and formaldehyde. Some of the aldehydes are commercially available as a polymer solution, an aqueous solution, or in the hydrated form. They can be used directly in the asymmetric aldol reaction as a commercially available form, which is a synthetic advantage. Given that the obtained aldol products possess several functional groups along with a formyl moiety, they are synthetically useful chiral building blocks. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15278999
- Volume :
- 23
- Issue :
- 7
- Database :
- Complementary Index
- Journal :
- Chemical Record
- Publication Type :
- Academic Journal
- Accession number :
- 164876070
- Full Text :
- https://doi.org/10.1002/tcr.202200159