No.106
Asymmetric Double Aldol Reactions
| A1535 | (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Acetate (1a) |
1g |
| A1534 | (1R,2S)-2-[N-Benzyl-N-(mesityl-enesulfonyl)amino]-1-phenylpropyl Acetate (1b) |
1g |
The aldol reactions of the acetate esters 1 and a variety of aldehydes provide bis-aldol products via novel double aldol reactions with high diastereoselectivity, which has been reported by A. Abiko, S. Masamune et al. These products 2 serve as the starting materials for the synthesis of chiral triols 3 of C3 symmetry. Compounds of C3 symmetry have attracted much attention as valuable ligands for asymmetric catalysts.
References
1) Boron-mediated double aldol reaction of carboxylic esters
A. Abiko, J.-F. Liu, D. C. Buske, S. Moriyama, S. Masamune, J. Am. Chem. Soc., 121, 7168 (1999).
2) C3 Symmetry in asymmetric catalysis and chiral recognition
C. Moberg, Angew. Chem. Int. Ed., 37, 248 (1998).
A. Abiko, J.-F. Liu, D. C. Buske, S. Moriyama, S. Masamune, J. Am. Chem. Soc., 121, 7168 (1999).
2) C3 Symmetry in asymmetric catalysis and chiral recognition
C. Moberg, Angew. Chem. Int. Ed., 37, 248 (1998).
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kdjoad000000407g
