Iridium-Catalyzed Synthesis of ω-Hydroxy Homoallylic Alcohols

Abstract

A novel process has been developed for the construction ω-hydroxy homoallylic alcohols via the iridium-catalyzed reaction of α,ω-diols with 2-alkynes such as 1-arylprop-1-ynes.

Key words

iridium catalyst - ω-hydroxy homoallylic alcohol - diol - transfer hydrogenation - 1-arylprop-1-yne

• References

• 1a Roulland E, Ermolenko MS. Org. Lett. 2005; 7: 2225
• 1b White JD, Quaranta L, Wang G. J. Org. Chem. 2007; 72: 1717
• 1c Yadav JS, Narasimhulu G, Reddy NM, Reddy BV. S. Tetrahedron Lett. 2010; 51: 1574
• 2 Nagano Y, Orita A, Otera J. Tetrahedron 2002; 58: 8211
• 3 Yadav JS, Chandrakanth D, Rao YG, Ravindar K, Reddy BV. S. Helv. Chim. Acta 2010; 93: 1432

For example:
• 4a Matsumoto K, Hashimoto K, Sakuragi M, Kusunoki A, Nogawa M. Lett. Org. Chem. 2011; 8: 536
• 4b Goto T, Utsunomiya S, Aiba H, Hayasaka H, Endo M, Watanabe R, Ishizaki T, Sato R, Saito M. Bull. Chem. Soc. Jpn. 1991; 64: 1901
• 4c Barluenga J, Fananas FJ, Yus M. J. Org. Chem. 1979; 44: 4798
• 4d Kyba EP, Siegel MG, Sousa LR, Sogah GD, Cram DJ. J. Am. Chem. Soc. 1973; 95: 2691

For selected reviews, see:
• 5a Ourida S, Williams JM. J. Top. Organomet. Chem. 2011; 34: 77
• 5b Zhang J, Leitus G, Ben-David Y, Milstein D. J. Am. Chem. Soc. 2005; 127: 10840
• 5c Hanasaka F, Fujita K, Yamaguchi R. Organometallics 2004; 23: 1490
• 5d Hamid MH. S. A, Slatford PA, Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555
• 5e Bower JF, Kim IS, Patman RL, Krische MJ. Angew. Chem. Int. Ed. 2009; 48: 34
• 5f Guillena G, Ramon DJ, Yus M. Chem. Rev. 2010; 110: 1611
• 5g Debereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
• 5h Takeuchi R, Kezuka S. Synthesis 2006; 3349

For selected examples, see:
• 6a Cho CS, Kim BT, Kim T.-J, Shim SC. J. Org. Chem. 2001; 66: 9020
• 6b Ndou AS, Plint N, Coville NJ. Appl. Catal., A 2003; 251: 337
• 6c Cho CS, Kim BT, Kim H.-S, Kim T.-J, Shim SC. Organometallics 2003; 22: 3608
• 6d Martínez R, Ramón DJ, Yus M. Tetrahedron 2006; 62: 8982
• 6e Fujita K, Asai C, Yamaguchi T, Hanasaka F, Yamaguchi R. Org. Lett. 2005; 7: 4017
• 6f Onodera G, Nishibayashi Y, Uemura S. Angew. Chem. Int. Ed. 2006; 45: 3819
• 6g Guillena G, Ramon DJ, Yus M. Angew. Chem. Int. Ed. 2007; 46: 2358
• 6h Nixon TD, Whittlesey MK, Williams JM. J. Dalton Trans. 2009; 753; and references cited therein
• 7a Taniguchi K, Nakagawa H, Hirabayashi T, Sakaguchi S, Ishii Y. J. Am. Chem. Soc. 2004; 126: 72
• 7b Maeda K, Obora Y, Sakaguchi S, Ishii Y. Bull. Chem. Soc. Jpn. 2008; 81: 689
• 7c Iuchi Y, Obora Y, Ishii Y. J. Am. Chem. Soc. 2010; 132: 2536
• 7d Morita M, Obora Y, Ishii Y. Chem. Commun. 2007; 2850
• 7e Obora Y, Anno Y, Okamoto R, Matsu-ura T, Ishii Y. Angew. Chem. Int. Ed. 2011; 50: 8618
• 7f Matsu-ura T, Sakaguchi S, Obora Y, Ishii Y. J. Org. Chem. 2006; 71: 8306
• 7g Obora Y, Ishii Y. Synlett 2011; 30
• 8a Obora Y, Hatanaka S, Ishii Y. Org. Lett. 2009; 11: 3510
• 8b Hatanaka S, Obora Y, Ishii Y. Chem. Eur. J. 2010; 16: 1883
• 9 Esteruelas MA, Hernandez YA, López AM, Oliván M, Oñate E. Organometallics 2007; 26: 2193
• 10a Burk MJ, Crabtree RH, McGrath DV. J. Chem. Soc., Chem. Commun. 1985; 1829
• 10b Gupta M, Hagen C, Kaska WC, Cramer RE, Jensen CM. J. Am. Chem. Soc. 1997; 119: 840
• 10c Liu F, Goldman AS. Chem. Commun. 1999; 655
• 11 Weiss HM, Touchette KM, Angell S, Khan J. Org. Biomol. Chem. 2003; 1: 2152