Boronic Acid Catalysis for Aza-Piancatelli Rearrangement

^‡ These authors contributed equally to this work

Abstract

A first example of boronic acid catalyzed intermolecular aza-Piancatelli rearrangement to access a wide range of trans-4,5-disubstituted cyclopentenones is described. The catalytic system can also be extended to intramolecular aza-Piancatelli rearrangement to afford a wide range of azaspirocycles. Good to excellent yields were obtained in an excellent diastereoselective manner.

Key words

boronic acid - aza-Piancatelli rearrangement - furylcarbinols - cyclopentenones - azaspirocycles

• References


For Nazarov reactions and Pauson–Khand reactions, see:
• 1a Santelli-Rouvier C. Santelli M. Synthesis 1983; 429
• 1b Habermas KL. Denmark SE. Jones TK. In Organic Reactions . Vol. 45. Paquette LA. Wiley; New York: 1994: 1-158
• 1c Harmata M. Chemtracts 2004; 17: 416
• 1d Pellissier H. Tetrahedron 2005; 61: 6479
• 1e Frontier AJ. Collison C. Tetrahedron 2005; 61: 7577
• 1f Tius MA. Eur. J. Org. Chem. 2005; 2193
• 1g Nakanishi N. West FG. Curr. Opin. Drug Discov. Dev. 2009; 12: 732
• 1h Shimada N. Stewart C. Tius MA. Tetrahedron 2011; 67: 5851
• 1i Vaidya T. Eisenberg R. Frontier AJ. ChemCatChem 2011; 3: 1531
• 1j Spencer WT. III. Vaidya T. Frontier AJ. Eur. J. Org. Chem. 2013; 3621
• 1k Tius MA. Chem. Soc. Rev. 2014; 43: 2979
• 1l Blanco-Urgoiti J. Anorbe L. Perez-Serrano L. Dominguez G. Perez-Castells J. Chem. Soc. Rev. 2004; 33: 32
• 1m Grant TN. Rieder CJ. West FG. Chem. Commun. 2009; 5676
• 1n Gibson SE. Mainolfi N. Angew. Chem. Int. Ed. 2005; 44: 3022
• 2a Piancatelli G. Scettri A. Barbadoro S. Tetrahedron Lett. 1976; 3555
• 2b Faza AN. Lopez CS. Alvarez R. de Lera IR. Chem. Eur. J. 2004; 10: 4324
• 2c Piancatelli G. Dauria M. Donofrio F. Synthesis 1994; 867

For recent examples, see:
• 3a Veits GK. Wenz DR. Read de Alaniz J. Angew. Chem. Int. Ed. 2010; 49: 9484
• 3b Palmer LI. Read de Alaniz J. Angew. Chem. Int. Ed. 2011; 50: 7167
• 3c Subba Reddy BV. Reddy YV. Lakshumma PS. Narasimhulu G. Yadav JS. Sridhar B. Reddy PP. Kunwar AC. RSC Adv. 2012; 2: 10661
• 3d Liu J. Shen Q. Yu J. Zhu M. Han J. Wang L. Eur. J. Org. Chem. 2012; 6933
• 3e Palmer LI. Read de Alaniz J. Org. Lett. 2013; 15: 476
• 3f Wenz DR. Read de Alaniz J. Org. Lett. 2013; 15: 3250
• 3g Yu D. Tahai VT. Palmer LI. Veits GK. Cook JE. Read de Alaniz J. Hein JE. J. Org. Chem. 2013; 78: 12784
• 3h Yin B. Huang L. Wang X. Liu J. Jiang H. Adv. Synth. Catal. 2013; 355: 370
• 3i Fisher D. Palmer LI. Cook JE. Davis JE. Read de Alaniz J. Tetrahedron 2014; 70: 4105
• 3j Lebœuf D. Schulz E. Gandon V. Org. Lett. 2014; 16: 6464
• 3k Li H. Tong R. Sun J. Angew. Chem. Int. Ed. 2016; 55: 15125
• 3l Cai Y. Tang Y. Atodiresei I. Rueping M. Angew. Chem. Int. Ed. 2016; 55: 14126
• 3m Xu Z.-L. Xing P. Jiang B. Org. Lett. 2017; 19: 1028
• 4a Jia F. Hong J. Sun P.-H. Chen J.-X. Chen W.-M. Synth. Commun. 2013; 43: 2641
• 4b Hanessian S. Vakiti RR. Dorich S. Banerjee S. Lecomte F. Del Valle JR. Zhang J. Deschenes-Simard B. Angew. Chem. Int. Ed. 2011; 50: 3497
• 4c Malinowski JT. Sharpe RJ. Johnson JS. Science 2013; 340: 180
• 4d Sharpe RJ. Malinowski JT. Johnson JS. J. Am. Chem. Soc. 2013; 135: 17990
• 4e Kobayashi Y. Miyazaki H. Shiozaki M. J. Am. Chem. Soc. 1992; 114: 10065
• 4f Ledford BE. Carreira EM. J. Am. Chem. Soc. 1995; 117: 11811

For reviews of BAC, see:
• 5a Dimitrijević E. Taylor MS. ACS Catal. 2013; 3: 945
• 5b Georgiou I. Ilyashenko G. Whiting A. Acc. Chem. Res. 2009; 42: 756
• 6a Al-Zoubi RM. Marion O. Hall DG. Angew. Chem. Int. Ed. 2008; 47: 2876
• 6b Zheng H. Hall DG. Tetrahedron Lett. 2010; 51: 3561
• 6c Zheng H. McDonald R. Hall DG. Chem. Eur. J. 2010; 16: 5454
• 6d Arnold K. Davies B. Hérault D. Whiting A. Angew. Chem. Int. Ed. 2008; 47: 2673
• 6e Aelvoet K. Batsanov AS. Blatch AJ. Grosjean C. Patrick LG. F. Smethurst CA. Whiting A. Angew. Chem. Int. Ed. 2008; 47: 768
• 6f Zheng H. Lejkowski M. Hall DG. Chem. Sci. 2011; 2: 1305
• 6g Zheng H. Lejkowski M. Hall DG. Tetrahedron Lett. 2013; 54: 91
• 6h Zheng H. Ghanbari S. Nakamura S. Hall DG. Angew. Chem. Int. Ed. 2012; 51: 6187
• 6i Soeta T. Kojima Y. Ukaji Y. Inomata K. Tetrahedron Lett. 2011; 52: 2557
• 6j McCubbin JA. Krokhin OV. Tetrahedron Lett. 2010; 51: 2447
• 6k McCubbin JA. Hosseini H. Krokhin OV. J. Org. Chem. 2010; 75: 959
• 6l Li M. Yang T. Dixon DJ. Chem. Commun. 2010; 46: 2191
• 6m Debache A. Boumoud B. Amimour M. Belfaitah A. Rhouati S. Carboni B. Tetrahedron Lett. 2006; 47: 5697
• 6n Rao G. Philipp M. J. Org. Chem. 1991; 56: 1505
• 6o Sakakura A. Ohkubo T. Yamashita R. Akakura M. Ishihara K. Org. Lett. 2011; 13: 892
• 6p Marcelli T. Angew. Chem. Int. Ed. 2010; 49: 6840
• 6q Ishihara K. Ohara S. Yamamoto H. J. Org. Chem. 1996; 61: 4196
• 6r Li Y. de La Torre JA. M. Grabow K. Bentrup U. Junge K. Zhou S. Brückner A. Beller M. Angew. Chem. Int. Ed. 2013; 52: 11577
• 6s Lee D. Taylor MS. J. Am. Chem. Soc. 2011; 133: 3724
• 6t William JM. Kuriyama M. Onomura O. Adv. Synth. Catal. 2014; 356: 934
• 6u Maki T. Ishihara K. Yamamoto H. Tetrahedron 2007; 63: 8645
• 7 Cao K.-S. Bian H.-X. Zheng W.-H. Org. Biomol. Chem. 2015; 13: 6449
• 8a Dake G. Tetrahedron 2006; 62: 3467
• 8b Auerbach J. Weinreb SM. J. Am. Chem. Soc. 1972; 94: 7172
• 8c Semmelhack MF. Chong BP. Jones LD. J. Am. Chem. Soc. 1972; 94: 8629
• 8d Eckelbarger JD. Wilmot JT. Gin DY. J. Am. Chem. Soc. 2006; 128: 10370
• 8e Taniguchi T. Tanabe G. Muraoka O. Ishibashi H. Org. Lett. 2008; 10: 197
• 8f Zhao Y.-M. Gu P. Tu Y.-Q. Fan C.-A. Zhang Q. Org. Lett. 2008; 10: 1763
• 8g Clive DL. J. Yu ML. Wang J. Yeh VS. C. Kang SZ. Chem. Rev. 2005; 105: 4483
• 8h Sinclair A. Stockman RA. Nat. Prod. Rep. 2007; 24: 298
• 8i Nilsson BL. Overman LE. Read de Alaniz J. Rohde JM. J. Am. Chem. Soc. 2008; 130: 11297
• 8j Cheng X. Waters SP. Org. Lett. 2010; 12: 205
• 9a Li S.-W. Batey RA. Chem. Commun. 2007; 3759
• 9b Duspara PA. Batey RA. Angew. Chem. Int. Ed. 2013; 52: 10862
• 9c Liu J. Yu J. Zhu M. Li J. Zheng X. Wang L. Synthesis 2013; 45: 2165