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Named reactions

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Protecting Groups

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Horner-Wadsworth-Emmons Reaction

Horner-Wadsworth-Emmons Reaction

Mechanism of the Horner-Wadsworth-Emmons Reaction

Reference

Original reference Chem. Ber. 1958, 91, 61.
Wikipedia link
Organic chemistry portal link


Sample reactions

This step is from the synthesis of Quinine by Eric N. Jacobsen. Show me the full synthesis.

Reactant structure + Reactant structure
n-BuLi
Reaction arrow head
THF
-78 to 0 °C, 2 h
84 %
Product structure

This step is from the synthesis of Quinine by Yuichi Kobayashi. Show me the full synthesis.

Reactant structure + Reactant structure
NaH
Reaction arrow head
THF
RT
82 %
Product structure

This step is from the synthesis of Prostaglandin F2α by Elias J. Corey. Show me the full synthesis.

Reactant structure + Reactant structure
NaH
Reaction arrow head
DME
RT, 60 min
70 % (2 steps)
Product structure

This step is from the synthesis of U-106305 by André B. Charette. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
THF
0 °C to RT, 12.5 h
49 % (2 steps)
Product structure

This step is from the synthesis of U-106305 by André B. Charette. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
THF
0 °C to RT, 12.5 h
41 % (2 steps)
Product structure

This step is from the synthesis of U-106305 by André B. Charette. Show me the full synthesis.

Reactant structure + Reactant structure
NaH
Reaction arrow head
DME
0 °C to RT, 5 h
80 %
Product structure

This step is from the synthesis of Elailoide by David A. Evans. Show me the full synthesis.

Reactant structure + Reactant structure
TMS2NLi
Reaction arrow head
THF
-78 °C, 12 h
85 %
Product structure

This step is from the synthesis of Ingenol by Isao Kuwajima. Show me the full synthesis.

Reactant structure + Reactant structure
n-BuLi
Reaction arrow head
THF, Et2O
-98 °C to RT, 3 h
85 %
Product structure

This step is from the synthesis of Epolactaene by Yujiro Hayashi. Show me the full synthesis.

Reactant structure + Reactant structure
NaH
Reaction arrow head
THF
0 °C to RT, 60 min
96 %
Product structure

This step is from the synthesis of Epolactaene by Yujiro Hayashi. Show me the full synthesis.

Reactant structure + Reactant structure
n-BuLi
Reaction arrow head
DME
0 °C to RT, 40 min
100 %
Product structure

This step is from the synthesis of Stigmatellin A by Dieter Enders. Show me the full synthesis.

Reactant structure + Reactant structure
NaH
Reaction arrow head
THF
-78 °C to RT, ON
71 %
Product structure

This step is from the synthesis of Stigmatellin A by Dieter Enders. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi
Reaction arrow head
THF
-78 °C to RT, ON
77 % (2 steps)
Product structure

This step is from the synthesis of Doliculide by Arun K. Ghosh. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
THF
0 °C to RT, 4 h
84 %
Product structure

This step is from the synthesis of Doliculide by Arun K. Ghosh. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
THF
0 °C to RT, 4 h
80 % (2 steps)
Product structure

This step is from the synthesis of Doliculide by Arun K. Ghosh. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
THF
0 °C to RT, 4 h
60 % (2 steps)
Product structure

This step is from the synthesis of Pallidol by Scott A. Snyder. Show me the full synthesis.

Reactant structure + Reactant structure
KOt-Bu
Reaction arrow head
THF
-78 °C to RT, 13.5 h
98 %
Product structure

This step is from the synthesis of Ampelopsin F by Scott A. Snyder. Show me the full synthesis.

Reactant structure + Reactant structure
KOt-Bu
Reaction arrow head
THF
-78 °C to RT, 13.5 h
98 %
Product structure

This step is from the synthesis of Retigeranic Acid by Tomas Hudlicky. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi, HMPA
Reaction arrow head
THF
-78 to 0 °C, 60 min
Product structure

This step is from the synthesis of Strychnine by Albert Padwa. Show me the full synthesis.

Reactant structure
Ph2P(O)CH2OMe, i-Pr2NLi
Reaction arrow head
THF
0 °C to RT, 25 h
72 %
Product structure

This step is from the synthesis of Strychnine by Philip Magnus. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CN, TMS2NK
Reaction arrow head
THF
RT, 42 h
43 %
Product structure

This step is from the synthesis of Strychnine by Martin E. Kuehne. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Me, TMS2NK
Reaction arrow head
THF
0 °C to RT, 8.5 h
64 %
Product structure

This step is from the synthesis of Strychnine by Martin E. Kuehne. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Me, TMS2NK
Reaction arrow head
THF
RT, 2.5 h
39 %
Product structure

This step is from the synthesis of Strychnine by David W. C. MacMillan. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2SeMe, TMS2NK, 18-Crown-6
Reaction arrow head
THF
-78 °C to RT, 90 min
81 %
Product structure

This step is from the synthesis of Nupharamine by Isao Shimizu. Show me the full synthesis.

Reactant structure + Reactant structure
NaH
Reaction arrow head
THF
0 °C
87 %
Product structure

This step is from the synthesis of Nupharamine by Roderick W. Bates. Show me the full synthesis.

Reactant structure + Reactant structure
Ba(OH)2
Reaction arrow head
THF, H2O
87 % (2 steps)
Product structure

This step is from the synthesis of Azadirachtin by Steven V. Ley. Show me the full synthesis.

Reactant structure + Reactant structure
LiCl, i-Pr2NEt
Reaction arrow head
DMF
RT, 44 h
34 %
Product structure

This step is from the synthesis of Epibatidine by David A. Evans. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NEt, LiCl
Reaction arrow head
MeCN
RT, 60 min
81 %
Product structure

This step is from the synthesis of Hirsutene by Tarun K. Sarkar. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
DME
RT, 3 h
76 %
Product structure

This step is from the synthesis of Decarestrictine D by Ronaldo A. Pilli. Show me the full synthesis.

Reactant structure
(EtO)2P(O)CH2CO2Et, NaH
Reaction arrow head
THF
0 °C
70 %
Product structure

This step is from the synthesis of Corynantheidol by Albert I. Meyers. Show me the full synthesis.

Reactant structure
(MeO)2P(O)CH2CO2Me, NaH
Reaction arrow head
THF
0 to 50 °C, 4.5 h
83 %
Product structure

This step is from the synthesis of Acromelobinic Acid by Maciej Adamczyk. Show me the full synthesis.

Reactant structure + Reactant structure
1,1,3,3-Tetramethylguanidine
Reaction arrow head
THF
0 °C to RT, 6 h
66 %
Product structure

This step is from the synthesis of Tirandamycin B by Philip DeShong. Show me the full synthesis.

Reactant structure + Reactant structure
KOt-Bu
Reaction arrow head
THF
0 °C, 18 h
72 %
Product structure

This step is from the synthesis of Phyllantidine by Michael A. Kerr. Show me the full synthesis.

Reactant structure
K2CO3, 18-Crown-6
Reaction arrow head
PhMe
RT, 2.5 h
100 %
Product structure
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