Regioselective Control of 1,2- Versus 1,4-Addition in Organocatalytic Reactions of o-Hydroxycinnamaldehydes with Organoboronic Acids

Abstract

The regioselective 1,2-addition and 1,4-addition reactions of o-hydroxycinnamaldehydes with organoboronic acids in the presence of organocatalysts gave 2-substituted 2H-chromenes and 4-substituted chroman-2-ols, respectively. Diethylamine was used as the catalyst for the 1,4-addition reaction, whereas dibenzyl­amine and trichloroacetic acid were used as the catalyst and additive, respectively, in the 1,2-addition reaction.

Key words

catalysis - addition reactions - heterocycles - regioselectivity - chromanols - chromenes

References

• 1a Sibi MP. Manyem S. Tetrahedron  2000,  56:  8033 
• 1b Tomioka K. Nagaoka Y. In Comprehensive Asymmetric Catalysis   Vol. III:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer; New York: 1999.  Chap. 31.
• For reviews on organocatalytic conjugate additions, see:
• 2a Almasi D. Alonso DA. Najera C. Tetrahedron: Asymmetry  2007,  18:  299 
• 2b Tsogoeva SB. Eur. J. Org. Chem.  2007,  1701 
• 3 Hayashi T. Yamasaki K. Chem. Rev.  2003,  103:  2829 
• 4a Lee S. MacMillan DWC. J. Am. Chem. Soc.  2007,  129:  15438 
• 4b Kim S.-G. Tetrahedron Lett.  2008,  49:  6148 
• 4c Inokuma T. Takasu K. Sakaeda T. Takemoto Y. Org. Lett.  2009,  11:  2425 
• 5a Ueda M. Miyaura N. J. Org. Chem.  2000,  65:  4450 
• 5b Soeta T. Kuriyama M. Tomioka K. J. Org. Chem.  2005,  70:  297 
• 5c Tomita D. Kanai M. Shibasaki M. Chem. Asian J.  2006,  1:  161 
• 5d Sakurai F. Kondo K. Aoyama T. Chem. Pharm. Bull.  2009,  57:  511 
• 6a Kim JH. Lee S. Kwon M.-G. Park YS. Choi S.-K. Kwon B.-M. Synth. Commun.  2004,  34:  1223 
• 6b Zeiter K. Rose CA. J. Org. Chem.  2009,  74:  1759 
• 7a Lockhart IM. In The Chemistry of Heterocyclic Compounds   Vol. 31:  Ellis GP. Wiley; New York: 2007.  p.1-1196  
• 7b Green GR. Evans JM. Vong AK. In Comprehensive Heterocyclic Chemistry II   Vol. 5:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.469-500  
• 7c Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
• For recent syntheses of 2H-chromenes, see:
• 8a Wang Q. Finn MG. Org. Lett.  2000,  2:  4063 
• 8b Liu F. Evans T. Das BC. Tetrahedron Lett.  2008,  49:  1578 
• 8c Patasis NA. Butkevich AN. J. Organomet. Chem.  2009,  694:  1747 
• 8d Das BC. Mohapatra S. Campbell PD. Nayak S. Mahalingam SM. Evans T. Tetrahedron Lett.  2010,  51:  2567 
• For recent synthesis of chroman-2-ols, see:
• 9a Selenski C. Pettus TRR. J. Org. Chem.  2004,  69:  9196 
• 9b Rueping M. Sugiono E. Merino E. Angew. Chem. Int. Ed.  2008,  47:  3046 
• 9c Rueping M. Merino E. Sugiono E. Adv. Synth. Catal.  2008,  350:  2127 
• 9d Gallagher BD. Taft BR. Lipshutz BH. Org. Lett.  2009,  11:  5374 
• 9e Hong L. Wang L. Sun W. Wong K. Wang R. J. Org. Chem.  2009,  74:  6881 
• 10 Choi K.-S. Kim S.-G. Tetrahedron Lett.  2010,  51:  5203 
• 11a Ouellet SG. Walji AM. MacMillan DWC. Acc. Chem. Res.  2007,  40:  1327 
• 11b Zu L. Zhang S. Xie H. Wang W. Org. Lett.  2009,  11:  1627 
• 12 Perrin DD. Armarego WLF. Perrin DR. Purification of Laboratory Chemicals   3rd ed.:  Butterworth-Heinemann; Oxford: 1996.