Asymmetric Inverse-Electron-Demand
Hetero-Diels-Alder Reaction via Enamine-Metal
Lewis Acid Bifunctional Catalysis

Zhenghu Xu; Hong Wang

doi:10.1055/s-0031-1289892

SYNPACTS

Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction via Enamine-Metal Lewis Acid Bifunctional Catalysis

Zhenghu Xu*^a, Hong Wang*^b
^a Key Lab of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong, University, No. 27 South Shanda Road, Jinan 250100, Shandong Province, P. R. of China
e-Mail: xuzh@sdu.edu.cn;
^b Department of Chemistry and Biochemistry, Miami University, 254 Hughes Laboratories, 701 E High Street, Oxford, OH 45056, USA
Fax: +1(513)5295715; e-Mail: wangh3@muohio.edu;

Abstract

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Abstract

This paper describes the development of an efficient and atom-economic asymmetric inverse-electron-demand hetero-Diels-Alder reaction of six-membered ketones with β,γ-unsaturated α-keto esters via enamine-metal Lewis acid bifunctional catalysis.

Key words

asymmetric catalysis - bifunctional catalysis - enamines - Lewis acids - ketones - Hetero-Diels-Alder reaction

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References

References and Notes

1a Pellissier H. Tetrahedron 2009, 65: 2839

1b Jorgensen KA. Eur. J. Org. Chem. 2004, 2093

1c Jorgensen KA. Johannsen M. Yao SL. Audrain H. Thorhauge J. Acc. Chem. Res. 1999, 32: 605

1d Alfini R. Cecchi M. Giomi D. Molecules 2010, 15: 1722

2a Juhl K. Jorgensen KA. Angew. Chem. Int. Ed. 2003, 42: 1498

2b Zhao Y. Wang XJ. Liu JT. Synlett 2008, 1017

2c Samanta S. Krause J. Mandal T. Zhao CG. Org. Lett. 2007, 9: 2745

2d Xie HX. Zu LS. Oueis HR. Wang HLJ. Wang W. Org. Lett. 2008, 10: 1923

2e Han B. He ZQ. Li JL. Li R. Jiang K. Liu TY. Chen YC. Angew. Chem. Int. Ed. 2009, 48: 5474

2f Han B. Li JL. Ma C. Zhang SJ. Chen YC. Angew. Chem. Int. Ed. 2008, 47: 9971

2g Wang J. Yu F. Zhang X. Ma D. Org. Lett. 2008, 10: 2561

3 Xu ZH. Liu L. Wheeler K. Wang H. Angew. Chem. Int. Ed. 2011, 50: 3484

4a Yanagisawa A. Arai T. Chem. Commun. 2008, 1165

4b Desimoni G. Faita G. Jorgensen KA. Chem. Rev. 2006, 106: 3561

4c Bartok M. Chem. Rev. 2010, 110: 1663

4d Jorgensen KA. Angew. Chem. Int. Ed. 2000, 39: 3558

5a Thorhauge J. Johannsen M. Jorgensen KA. Angew. Chem. Int. Ed. 1998, 37: 2404

5b Evans DA. Johnson JS. J. Am. Chem. Soc. 1998, 120: 4895

5c Evans DA. Olhava EJ. Johnson JS. Janey JM. Angew. Chem. Int. Ed. 1998, 37: 3372

5d Evans DA. Johnson JS. Olhava EJ. J. Am. Chem. Soc. 2000, 122: 1635

5e Jørgensen KA. Angew. Chem. Int. Ed. 2000, 39: 3558

5f Gademann K. Chavez DE. Jacobsen EN. Angew. Chem. Int. Ed. 2002, 41: 3059

6 Esquivias J. Arrayas RG. Carretero JC. J. Am. Chem. Soc. 2007, 129: 1480

7 Li P. Yamamoto H. J. Am. Chem. Soc. 2009, 131: 16628

8 Gallier F. Hussain H. Martel A. Kirschning A. Dujardin G. Org. Lett. 2009, 11: 3060

9a Zheng C. Wu Y. Wang X. Zhao G. Adv. Synth. Catal. 2008, 350: 2690

9b Cao CL. Sun XL. Kang YB. Tang Y. Org. Lett. 2007, 9: 4151

For reviews, see

10a Shao ZH. Zhang HB. Chem. Soc. Rev. 2009, 38: 2745

10b Zhong C. Shi XD. Eur. J. Org. Chem. 2010, 2999

For examples, see:

10c Allen AE. MacMillan DWC. J. Am. Chem. Soc. 2010, 132: 4986

10d Yang T. Ferrali A. Campbell L. Dixon DJ. Chem. Commun. 2008, 2923

10e Ding QP. Wu J. Org. Lett. 2007, 9: 4959

10f Ibrahem I. Cordova A. Angew. Chem. Int. Ed. 2006, 45: 1952

10g Bihelovic F. Matovic R. Vulovic B. Saicic RN. Org. Lett. 2007, 9: 5063

10h Usui I. Schmidt S. Breit B. Org. Lett. 2009, 11: 1453

10i Lin SZ. Zhao GL. Deiana L. Sun JL. Zhang QO. Leijonmarck H. Cordova A. Chem. Eur. J. 2010, 16: 13930

10j Hashmi ASK. Hubbert C. Angew. Chem. Int. Ed. 2010, 49: 1010

10k Binder JT. Crone B. Haug TT. Menz H. Kirsch SF. Org. Lett. 2008, 10: 1025

10l Ikeda M. Miyake Y. Nishibayashi Y. Angew. Chem. Int. Ed. 2010, 49: 7289

10m Abillard O. Breit B. Adv. Synth. Catal. 2007, 349: 1891

10n Chercheja S. Eilbracht P. Adv. Synth. Catal. 2007, 349: 1897

10o Quintard A. Alexakis A. Mazet C. Angew. Chem. Int. Ed. 2011, 50: 2354

10p Kemme ST. Smejkal T. Breit B. Chem. Eur. J. 2010, 16: 3423

10q Abillard O. Breit B. Adv. Synth. Catal. 2007, 349: 1891

10r Chercheja S. Eilbracht P. Adv. Synth. Catal. 2007, 349: 1897

10s Nicewicz DA. MacMillan DWC. Science 2008, 322: 77

10t Nagib DA. Scott ME. MacMillan DWC. J. Am. Chem. Soc. 2009, 131: 10875

11

Other types of catalytic systems combining enamine catalysis with metal catalysis have also been reported recently. In these systems, the enamine catalysis and
the metal catalysis occur in sequence, see refs. 10o-t

12a Paull DH. Abraham CJ. Scerba MT. Alden-Danforth E. Lectka T. Acc. Chem. Res. 2008, 41: 655

12b Groger H. Chem. Eur. J. 2001, 7: 5247

12c Wu LY. Bencivenni G. Mancinelli M. Mazzanti A. Bartoli G. Melchiorre P. Angew. Chem. Int. Ed. 2009, 48: 7196

12d Kanai M. Kato N. Ichikawa E. Shibasaki M. Synlett 2005, 1491

Although it was not clearly defined as enamine-metal Lewis acid bifunctional catalysts, the first example of the combination of an organo-amine catalyst with a metal salt through a chelating ligand was reported by the Mlynarski group. For details, see:

13a Paradowska J. Stodulski M. Mlynarski J. Adv. Synth. Catal. 2007, 349: 1041

13b Pasternak M. Paradowska J. Rogozinska M. Mlynarski J. Tetrahedron Lett. 2010, 51: 4088

13c Mlynarski J. Paradowska J. Chem. Soc. Rev. 2008, 37: 1502

13d Paradowska J. Stodulski M. Mlynarski J. Angew. Chem. Int. Ed. 2009, 48: 4288

14a Xu ZH. Daka P. Wang H. Chem. Commun. 2009, 6825

14b Xu ZH. Daka P. Budik I. Wang H. Bai FQ. Zhang HX. Eur. J. Org. Chem. 2009, 4581

14c Daka P. Xu ZH. Alexa A. Wang H. Chem. Commun. 2011, 47: 224