Stereoselective synthesis of β-substituted α, β-unsaturated esters by dialkylcuprate coupling to the enol phosphate of β-keto esters

1979 ◽  
Vol 57 (22) ◽  
pp. 2895-2895
Author(s):  
Fuk-Wah Sum ◽  
Larry Weiler
Keyword(s):  
Stereoselective Synthesis ◽  
Unsaturated Esters ◽  
Keto Esters ◽  
Enol Phosphate

not available

Stereoselective synthesis of β-substituted α,β-unsaturated esters by dialkylcuprate coupling to the enol phosphate of β-keto esters

1979 ◽  
Vol 57 (12) ◽  
pp. 1431-1441 ◽  
Author(s):  
Fuk-Wah Sum ◽  
Larry Weiler
Keyword(s):  
Good Yield ◽  
Stereoselective Synthesis ◽  
Unsaturated Esters ◽  
Keto Esters ◽  
Tetrasubstituted Olefins ◽  
Enol Phosphate

The anions from β-keto esters or β-diketones were reacted with diethyl phosphorochloridate to yield the corresponding enol phosphates. These enol phosphates were coupled with dialkylcuprates to produce the β-substituted α,β-unsaturated esters or ketones in good yield. Starting from acyclic β-keto esters this sequence was used to stereoselectively generate tri- and tetrasubstituted olefins.

syn-Selective Reformatsky-Type Reaction of α-Silyl-α-stannylacetic Esters with Aldehydes: Stereoselective Synthesis of (E)- and (Z)-α,β-Unsaturated Esters

Synlett ◽  
1991 ◽  
Vol 1991 (12) ◽  
pp. 911-912 ◽  
Author(s):  
Shuji Akai ◽  
Yasunori Tsuzuki ◽  
Satoshi Matsuda ◽  
Shinji Kitagaki ◽  
Yasuyuki Kita
Keyword(s):  
Stereoselective Synthesis ◽  
Unsaturated Esters ◽  
Type Reaction

ChemInform Abstract: Stereoselective Synthesis of (2Z)-α-Bromo-α,β- Unsaturated Esters via Arsonium Ylide.

ChemInform ◽  
2010 ◽  
Vol 27 (24) ◽  
pp. no-no
Author(s):  
Z.-Z. HUANG ◽  
L.-L. WU ◽  
L.-S. ZHU ◽  
X. HUANG
Keyword(s):  
Stereoselective Synthesis ◽  
Unsaturated Esters
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