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

Kwang-Su Choi; Sung-Gon Kim

doi:10.1055/s-0030-1258268

PAPER

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

Kwang-Su Choi, Sung-Gon Kim*
Department of Chemistry, College of Natural Science, Kyonggi University, San 94-6, Iui-dong, Yeongtong-gu, Suwon, 443-760, Republic of Korea
Fax: +82(31)2499631; e-Mail: sgkim123@kgu.ac.kr;

Abstract

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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

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References

<A NAME="RF13310SS-1A">1a</A> Sibi MP. Manyem S. Tetrahedron 2000, 56: 8033

<A NAME="RF13310SS-1B">1b</A> 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:

<A NAME="RF13310SS-2A">2a</A> Almasi D. Alonso DA. Najera C. Tetrahedron: Asymmetry 2007, 18: 299

<A NAME="RF13310SS-2B">2b</A> Tsogoeva SB. Eur. J. Org. Chem. 2007, 1701

<A NAME="RF13310SS-3">3</A> Hayashi T. Yamasaki K. Chem. Rev. 2003, 103: 2829

<A NAME="RF13310SS-4A">4a</A> Lee S. MacMillan DWC. J. Am. Chem. Soc. 2007, 129: 15438

<A NAME="RF13310SS-4B">4b</A> Kim S.-G. Tetrahedron Lett. 2008, 49: 6148

<A NAME="RF13310SS-4C">4c</A> Inokuma T. Takasu K. Sakaeda T. Takemoto Y. Org. Lett. 2009, 11: 2425

<A NAME="RF13310SS-5A">5a</A> Ueda M. Miyaura N. J. Org. Chem. 2000, 65: 4450

<A NAME="RF13310SS-5B">5b</A> Soeta T. Kuriyama M. Tomioka K. J. Org. Chem. 2005, 70: 297

<A NAME="RF13310SS-5C">5c</A> Tomita D. Kanai M. Shibasaki M. Chem. Asian J. 2006, 1: 161

<A NAME="RF13310SS-5D">5d</A> Sakurai F. Kondo K. Aoyama T. Chem. Pharm. Bull. 2009, 57: 511

<A NAME="RF13310SS-6A">6a</A> Kim JH. Lee S. Kwon M.-G. Park YS. Choi S.-K. Kwon B.-M. Synth. Commun. 2004, 34: 1223

<A NAME="RF13310SS-6B">6b</A> Zeiter K. Rose CA. J. Org. Chem. 2009, 74: 1759

<A NAME="RF13310SS-7A">7a</A> Lockhart IM. In The Chemistry of Heterocyclic Compounds Vol. 31: Ellis GP. Wiley; New York: 2007. p.1-1196

<A NAME="RF13310SS-7B">7b</A> 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

<A NAME="RF13310SS-7C">7c</A> Horton DA. Bourne GT. Smythe ML. Chem. Rev. 2003, 103: 893

For recent syntheses of 2H-chromenes, see:

<A NAME="RF13310SS-8A">8a</A> Wang Q. Finn MG. Org. Lett. 2000, 2: 4063

<A NAME="RF13310SS-8B">8b</A> Liu F. Evans T. Das BC. Tetrahedron Lett. 2008, 49: 1578

<A NAME="RF13310SS-8C">8c</A> Patasis NA. Butkevich AN. J. Organomet. Chem. 2009, 694: 1747

<A NAME="RF13310SS-8D">8d</A> 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:

<A NAME="RF13310SS-9A">9a</A> Selenski C. Pettus TRR. J. Org. Chem. 2004, 69: 9196

<A NAME="RF13310SS-9B">9b</A> Rueping M. Sugiono E. Merino E. Angew. Chem. Int. Ed. 2008, 47: 3046

<A NAME="RF13310SS-9C">9c</A> Rueping M. Merino E. Sugiono E. Adv. Synth. Catal. 2008, 350: 2127

<A NAME="RF13310SS-9D">9d</A> Gallagher BD. Taft BR. Lipshutz BH. Org. Lett. 2009, 11: 5374

<A NAME="RF13310SS-9E">9e</A> Hong L. Wang L. Sun W. Wong K. Wang R. J. Org. Chem. 2009, 74: 6881

<A NAME="RF13310SS-10">10</A> Choi K.-S. Kim S.-G. Tetrahedron Lett. 2010, 51: 5203

<A NAME="RF13310SS-11A">11a</A> Ouellet SG. Walji AM. MacMillan DWC. Acc. Chem. Res. 2007, 40: 1327

<A NAME="RF13310SS-11B">11b</A> Zu L. Zhang S. Xie H. Wang W. Org. Lett. 2009, 11: 1627

<A NAME="RF13310SS-12">12</A> Perrin DD. Armarego WLF. Perrin DR. Purification of Laboratory Chemicals 3rd ed.: Butterworth-Heinemann; Oxford: 1996.