Home > Community > How can I prepare a racemate of Henry reaction between...
Upvote

29

Downvote
+ Stereochemistry
Posted by
Aidan Cooney

How can I prepare a racemate of Henry reaction between...

Diana Smith  Follow

The classic way is to form a nitronate and then add the aldehyde.
Simply workup up the reaction by adding ammonium chloride instead of HCl and extract with EtOAc if you want the hydroxy nitro group.
http://orgsyn.org/Content/pdfs/procedures/CV1P0413.pdf

More

Upvote

VOTE

Downvote
Dave LaFrenere  Follow

Ugale,
I would like to add
---  Kopylovich, Maximilian N. et al,  Chemistry - A European Journal, 19(2), 588-600; 2013.
---  Uchida, Natsuko et al,  Journal of Organic Chemistry, 77(23), 10631-10637; 2012
--- Liu, Yu-Yu et al,  Chinese Journal of Chemistry, 26(12), 2267-2272; 2008
---  Wang, Xiu et al, Tetrahedron Letters, 49(45), 6442-6444; 2008
---  Jammi, Suribabu et al, Chemistry - An Asian Journal, 4(2), 314-320; 2009
--- Kantam, M. Lakshmi et al, Advanced Synthesis & Catalysis, 348(4 + 5), 569-578; 2006
--- Veisi, Hojat et al, Tetrahedron Letters, 55(38), 5311-5314; 2014
--- Uchida, Natsuko et al, Journal of Organic Chemistry, 77(23), 10631-10637; 2012
--- Phukan, Mridula et al, Green Chemistry Letters and Reviews, 2(4), 249-253; 2009
Good luck

More

Upvote

VOTE

Downvote
Donald Micheal Graham  Follow

Ajay Jakhar , Can I get the procedure or the refrence for it ?

More

Upvote

VOTE

Downvote
Axel Carlson  Follow

The classic way is to form a nitronate and then add the aldehyde.
Simply workup up the reaction by adding ammonium chloride instead of HCl and extract with EtOAc if you want the hydroxy nitro group.
http://orgsyn.org/Content/pdfs/procedures/CV1P0413.pdf

More

Upvote

VOTE

Downvote
David Hague  Follow

You may read:
Frederick A. Luzzio, The Henry reaction: recent examples, Tetrahedron 57 (2001) 915-945.

More

Upvote

VOTE

Downvote
Bob Given  Follow

You can easily prepare racamic nitro aldol product by using triethylamine.

More

Upvote

VOTE

Downvote