Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

2018 ◽  
Vol 54 (4) ◽  
pp. 374-377 ◽  
Author(s):  
Takahiro Kawajiri ◽  
Reiya Ohta ◽  
Hiromichi Fujioka ◽  
Hironao Sajiki ◽  
Yoshinari Sawama
Keyword(s):  
Aromatic Aldehyde ◽  
Aldol Reaction ◽  
Aliphatic Aldehydes ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Aldol Addition

Unprecedented chemoselectivity between aromatic and aliphatic aldehydes has been achieved in the Mukaiyama aldol reaction using aldehyde-derived silyl enol ethers.

Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins

2019 ◽  
Vol 55 (44) ◽  
pp. 6309-6312 ◽  
Author(s):  
Jindong Li ◽  
Yanan Li ◽  
Jianan Sun ◽  
Yang Gui ◽  
Yekai Huang ◽  
...  
Keyword(s):  
Aldol Reaction ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
High Yields

A highly enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins was developed. A series of chiral 3-substituted 3-hydroxy-2-oxindoles could be obtained exclusively with high yields (up to 95%) and excellent enantioselectivities (up to 99%). In particular, water was essential to improve the diastereoselectivity.

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