2006
DOI: 10.1021/ol061418q
|View full text |Cite
|
Sign up to set email alerts
|

Highly Efficient and Reusable Dendritic Catalysts Derived fromN-Prolylsulfonamide for the Asymmetric Direct Aldol Reaction in Water

Abstract: The direct aldol reactions catalyzed by chiral dendritic catalysts derived from N-prolylsulfonamide gave the corresponding products in high isolated yields (up to 99%) with excellent anti diastereoselectivities (up to >99:1) and enantioselectivities (up to >99% ee) in water. In addition, catalyst 1e may be recovered by precipitation and filtration and reused for at least five times without loss of catalytic activity.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1
1

Citation Types

1
58
0

Year Published

2008
2008
2012
2012

Publication Types

Select...
5
4
1

Relationship

0
10

Authors

Journals

citations
Cited by 249 publications
(59 citation statements)
references
References 35 publications
1
58
0
Order By: Relevance
“…More importantly, the catalyst could be recovered and reused for six times with maintained stereoselectivity. Wang and co-workers have synthesized various dendritic catalysts derived from N-prolylsulfonamide for the direct aldol reaction of cyclohexanone [21]. The dendritic catalyst could be recovered and reused at least five times without loss of catalytic activity and stereoselectivity.…”
Section: Asymmetric Aldol Reactionsmentioning
confidence: 99%
“…More importantly, the catalyst could be recovered and reused for six times with maintained stereoselectivity. Wang and co-workers have synthesized various dendritic catalysts derived from N-prolylsulfonamide for the direct aldol reaction of cyclohexanone [21]. The dendritic catalyst could be recovered and reused at least five times without loss of catalytic activity and stereoselectivity.…”
Section: Asymmetric Aldol Reactionsmentioning
confidence: 99%
“…131 Using the reaction shown in eq 84, the dendritic catalysts 77a, 77b, and 77c were compared one to another and to a low molecular weight N-prolylsulfonamide.…”
Section: Dendrimer-supported Organocatalystsmentioning
confidence: 99%
“…Barbas discovered that L-proline may be used as the catalyst for the direct asymmetric aldol reaction, 8 many groups have developed various proline-based organocatalysts [9][10][11][12][13][14][15] for the direct asymmetric aldol reaction. Among them, N-terminal prolyl dipeptides are effective for the direct catalytic asymmetric aldol reaction.…”
Section: Asymmetric Catalysismentioning
confidence: 99%