Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Sulfonamides

Guo-Fa Dai; Yu-Chuan Song; Fanhua Xiao; Wei-Liang Duan

doi:10.1055/s-0036-1591593

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(17): 3506-3512
DOI: 10.1055/s-0036-1591593

paper

Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Sulfonamides

Guo-Fa Dai

^aSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China eMail: fhxiao@sit.edu.cn

,

Yu-Chuan Song

^aSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China eMail: fhxiao@sit.edu.cn

,

Fanhua Xiao*

^aSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China eMail: fhxiao@sit.edu.cn

,

Wei-Liang Duan*

^bSchool of Chemistry and Chemical Engineering, Yangzhou University, No. 180 Siwangting Road, Yangzhou 225002, Jiangsu Province, P. R. of China eMail: duanwl@yzu.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A pincer palladium-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated sulfonamides was realized for the synthesis of chiral sulfonamide phosphines with up to 98% ee under mild conditions.

Key words

α,β-unsaturated sulfonamides - asymmetric 1,4-addition - pincer palladium catalyst - chiral phosphine

Volltext

Referenzen

References
1 Catalytic Asymmetric Conjugate Reactions . Córdova A. Wiley-VCH; Weinheim: 2010

For reviews on asymmetric 1,4-addition reactions, see:

2a Hayashi T. Yamasaki K. Chem. Rev. 2003; 103: 2829
2b Christoffers J. Koripelly G. Rosiak A. Rössle M. Synthesis 2007; 1279
2c Tsogoeva SB. Eur. J. Org. Chem. 2007; 1701
2d Enders D. Lüttgen K. Narine AA. Synthesis 2007; 959
2e Vicario JL. Badía D. Carrillo L. Synthesis 2007; 2065
2f Nising CF. Bräse S. Chem. Soc. Rev. 2008; 37: 1218
2g Miyaura N. Synlett 2009; 2039
2h Enders D. Wang C. Liebich JX. Chem. Eur. J. 2009; 15: 11058

For a review, see:

3a Nielsen M. Jacobsen CB. Holub N. Paixão MW. Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 2668

For selected examples of asymmetric nucleophilic addition to α,β-unsaturated sulfonyl compounds, see:

3b Mauleón P. Carretero JC. Org. Lett. 2004; 6: 3195
3c Mauleón P. Carretero JC. Chem. Commun. 2005; 4961
3d Mauleón P. Alonso I. Rivero MR. Carretero JC. J. Org. Chem. 2007; 72: 9924
3e Desrosiers JN. Bechara WS. Charette AB. Org. Lett. 2008; 10: 2315
3f Bos PH. Minnaard AJ. Feringa BL. Org. Lett. 2008; 10: 4219
3g Llamas T. Arrayás RG. Carretero JC. Angew. Chem. Int. Ed. 2007; 46: 3329
3h Desrosiers J.-N. Charette AB. Angew. Chem. Int. Ed. 2007; 46: 5955
3i Moure AL. Arrayas RG. Carretero JC. Chem. Commun. 2011; 4701
3j Nishimura T. Takiguchi Y. Hayashi T. J. Am. Chem. Soc. 2012; 134: 9086

For reviews on catalytic asymmetric synthesis of chiral phosphanes, see:

4a Glueck DS. Synlett 2007; 2627
4b Glueck DS. Chem. Eur. J. 2008; 14: 7108
4c Harvey JS. Gouverneur V. Chem. Commun. 2010; 7477
4d Zhao D. Wang R. Chem. Soc. Rev. 2012; 41: 2095
4e Rosenberg L. ACS Catal. 2013; 3: 2845
4f Koshti V. Gaikwad S. Chikkali SH. Coord. Chem. Rev. 2014; 265: 52
4g Jonathan R. Leung P.-H. Chem. Rec. 2016; 16: 141
4h Pullarkat SA. Synthesis 2016; 48: 493
4i Li Z. Duan W. Chin. J. Org. Chem. 2016; 36: 1805

For leading examples, see:

4j Kovacik I. Wicht DK. Grewal NS. Glueck DS. Incarvito CD. Guzei IA. Rheingold AL. Organometallics 2000; 19: 950
4k Scriban C. Kovacik I. Glueck DS. Organometallics 2005; 24: 4871
4l Sadow AD. Haller I. Fadini L. Togni A. J. Am. Chem. Soc. 2004; 126: 14704
4m Butti P. Rochat R. Sadow AD. Togni A. Angew. Chem. Int. Ed. 2008; 47: 4878
4n Moncarz JR. Laritcheva NF. Glueck DS. J. Am. Chem. Soc. 2002; 124: 13356
4o Blank NF. Moncarz JR. Brunker TJ. Scriban C. Anderson BJ. Amir O. Glueck DS. Zakharov LN. Golen JA. Incarvito CD. Rheingold AL. J. Am. Chem. Soc. 2007; 129: 6847
4p Chan VS. Bergman RG. Toste FD. J. Am. Chem. Soc. 2007; 129: 15122
4q Chan VS. Stewart IC. Bergman RG. Toste FD. J. Am. Chem. Soc. 2006; 128: 2786
4r Scriban C. Glueck DS. J. Am. Chem. Soc. 2006; 128: 2788
4s Chan VS. Chiu M. Bergman RG. Toste FD. J. Am. Chem. Soc. 2009; 131: 6021
4t Hong L. Sun W. Liu C. Zhao D. Wang R. Chem. Commun. 2010; 2856
4u Sun W. Hong L. Liu C. Wang R. Org. Lett. 2010; 12: 3914

For catalytic asymmetric 1,4-addition of substituted phosphines or phosphine oxides to electron-deficient alkenes, see:

5a Carlone A. Bartoli G. Bosco M. Sambri L. Melchiorre P. Angew. Chem. Int. Ed. 2007; 46: 4504
5b Ibrahem I. Rios R. Vesely J. Hammar P. Eriksson L. Himo F. Córdova A. Angew. Chem. Int. Ed. 2007; 46: 4507
5c Bartoli G. Bosco M. Carlone A. Locatelli M. Mazzanti A. Sambri L. Melchiorre P. Chem. Commun. 2007; 722
5d Fu X. Jiang Z. Tan C.-H. Chem. Commun. 2007; 5058
5e Ibrahem I. Hammar P. Vesely J. Rios R. Eriksso L. Córdova A. Adv. Synth. Catal. 2008; 350: 1875
5f Zhao D. Mao L. Yang D. Wang R. J. Org. Chem. 2010; 75: 6756
5g Wen S. Li L. Wu H. Yu F. Liang X. Ye J. Chem. Commun. 2010; 4806
5h Huang Y. Pullarkat SA. Li L. Leung P.-H. Chem. Commun. 2010; 6950
5i Russo A. Lattanzi A. Eur. J. Org. Chem. 2010; 6736
5j Luo X. Zhou Z. Li X. Liang X. Ye J. RSC Adv. 2011; 1: 698
5k Yang M.-J. Liu Y.-J. Gong J.-F. Song M.-P. Organometallics 2011; 30: 3793
5l Huang Y. Chew RJ. Li Y. Pullarkat SA. Leung P.-H. Org. Lett. 2011; 13: 5862
5m Huang Y. Pullarkat SA. Li Y. Leung P.-H. Inorg. Chem. 2012; 51: 2533
5n Zhao D. Wang L. Yang D. Zhang Y. Wang R. Chem. Asian J. 2012; 7: 881
5o Huang Y. Pullarkat SA. Teong S. Chew RJ. Li Y. Leung P.-H. Organometallics 2012; 31: 4871
5p Huang Y. Pullarkat SA. Chew RJ. Li Y. Leung P.-H. J. Org. Chem. 2012; 77: 6894
5q Hatano M. Horibe T. Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 4549
5r Chew RJ. Huang Y. Li Y. Pullarkat SA. Leung P.-H. Adv. Synth. Catal. 2013; 355: 1403
5s Ding B. Zhang Z. Xu Y. Liu Y. Sugiya M. Imamoto T. Zhang W. Org. Lett. 2013; 15: 5476
5t Chew RJ. Teo KY. Huang Y. Li B.-B. Li Y. Pullarkat SA. Leung P.-H. Chem. Commun. 2014; 8768
5u Chew RJ. Lu Y. Jia Y.-X. Li B.-B. Wong EH. Y. Goh R. Li Y. Huang Y. Pullarkat SA. Leung P.-H. Chem. Eur. J. 2014; 20: 14514
5v Hao X.-Q. Zhao Y.-W. Yang J.-J. Niu J.-L. Gong J.-F. Song M.-P. Organometallics 2014; 33: 1801
5w Hao X.-Q. Huang J.-J. Wang T. Lv J. Gong J.-F. Song M.-P. J. Org. Chem. 2014; 79: 9512
5x Xu Y. Yang Z. Ding B. Liu D. Liu Y. Sugiya M. Imamoto T. Zhang W. Tetrahedron 2015; 71: 6832
5y Yang X.-Y. Tay WS. Li Y. Pullarkat SA. Leung P.-H. Chem. Commun. 2016; 4211
5z Li X.-R. Yang X.-Y. Li Y. Pullarkat SA. Leung P.-H. Dalton Trans. 2017; 1311

6a Feng J.-J. Chen X.-F. Shi M. Duan W.-L. J. Am. Chem. Soc. 2010; 132: 5562
6b Du D. Duan W.-L. Chem. Commun. 2011; 11101
6c Chen Y.-R. Duan W.-L. Org. Lett. 2011; 13: 5824
6d Feng J.-J. Huang M. Lin Z.-Q. Duan W.-L. Adv. Synth. Catal. 2012; 354: 3122
6e Huang M. Li C. Duan W.-L. Xu S. Chem. Commun. 2012; 11148
6f Du D. Lin Z.-Q. Lu J.-Z. Li C. Duan W.-L. Asian J. Org. Chem. 2013; 2: 392
6g Lu J. Ye J. Duan W.-L. Chem. Commun. 2014; 698
6h Li C. Li W.-X. Xu S. Duan W.-L. Org. Chem. Front. 2014; 1: 541
6i Chen Y.-R. Feng J.-J. Duan W.-L. Tetrahedron Lett. 2014; 55: 595
6j Song Y.-C. Dai G.-F. Xiao F. Duan W.-L. Tetrahedron Lett. 2016; 57: 2990
6k Wei X. Duan W.-L. Synthesis 2016; 48: 4155

7 Lu J. Ye J. Duan W.-L. Org. Lett. 2013; 15: 5016
8 Chew RJ. Sepp K. Li B.-B. Li Y. Zhu P.-C. Tan NS. Leung P.-H. Adv. Synth. Catal. 2015; 357: 3297

9a Avan I. Tala SR. Steel PJ. Katritzky AR. J. Org. Chem. 2011; 76: 4884
9b Katritzky AR. He H.-Y. Suzuki K. J. Org. Chem. 2000; 65: 8210
9c Katritzky AR. Shestopalov AA. Suzuki K. Synthesis 2004; 1806

For synthesis and application of the chiral PCP–PdCl complex, see:

10a Longmire JM. Zhang X. Tetrahedron Lett. 1997; 38: 1725
10b Longmire JM. Zhang X. Shang M. Organometallics 1998; 17: 4374

Zusatzmaterial