Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides

Tianyun Zhou; Jigang Gao; Guofeng Liu; Xukai Guan; Dong An; Suoqin Zhang; Guangliang Zhang

doi:10.1055/s-0037-1610232

Synlett, Table of Contents

Synlett 2018; 29(15): 2006-2010
DOI: 10.1055/s-0037-1610232

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Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides

Tianyun Zhou

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

^bKey Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China

,

Jigang Gao

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

,

Guofeng Liu

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

,

Xukai Guan

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

,

Dong An

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

,

Suoqin Zhang*

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

^bKey Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China

,

Guangliang Zhang*

^aCollege of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China Email: zhgl_jl@jlu.edu.cn Email: suoqin@jlu.edu.cn

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Abstract

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Abstract

Chiral butenolides were synthesized by the enantioselective vinylogous Mannich reaction. Chiral (VAPOL)-type imidodiphosphoric acids are efficient catalysts for the asymmetric vinylogous Mannich (AVM) reaction of aldimines and trimethylsiloxyfuran in toluene. Under the optimized conditions, a series of butenolides were obtained with high yields (up to 98%) and enantioselectivities (up to 97% ee) as well as excellent diastereoselectivities (up to 99:1 dr).

Key words

butenolides - trimethylsiloxyfuran - organocatalysis - enantioselectivity - asymmetric vinylogous Mannich reaction

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References

References and Notes
1 Langer P. Synlett 2006; 3369
2 Kitani S. Miyamoto KT. Takamatsu S. Herawati E. Igucgi H. Nishitomi K. Uchida M. Nagamitsu T. Omura S. Ikeda H. Nihira T. Proc. Natl. Acad. Sci. USA 2011; 108: 16410
3 Lone SH. Bhat KA. Khuroo MA. Chem. Biol. Interact. 2015; 240: 180
4 Ottow EA. Brinker M. Teichmann T. Fritz E. Kaiser W. Brosché M. Kangasjärvi J. Jiang X. Polle A. Plant Physiol. 2005; 139: 1762
5 Mao B. Mastral MF. Feringa BL. Chem. Rev. 2017; 117: 10502

6a Mandai H. Mandai K. Snapper ML. Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 17961
6b Zhao Q.-Y. Shi M. Tetrahedron 2011; 67: 3724
6c Shi Y.-H. Wang Z. Shi Y. Deng W.-P. Tetrahedron 2012; 68: 3649
6d Silverio DL. Fu P. Carswell EL. Snapper ML. Hoveyda AH. Tetrahedron Lett. 2015; 56: 3489
6e Rainoldi G. Sacchetti A. Silvani A. Lesma G. Org. Biomol. Chem. 2016; 14: 7768

7 Martin SF. Lopez OD. Tetrahedron Lett. 1999; 40: 8949

8a Zhang Q. Hui Y. Zhou X. Lin L. Liu X. Feng X. Adv. Synth. Catal. 2010; 352: 976
8b Zhou L. Lin L. Ji J. Xie M. Liu X. Feng X. Org. Lett. 2011; 13: 3056
8c Ruan S.-T. Luo J.-M. Du Y. Huang P.-Q. Org. Lett. 2011; 13: 4938
8d Ranieri B. Curti C. Battistini L. Sartori A. Pinna L. Casiraghi G. Zanardi F. J. Org. Chem. 2011; 76: 10291

9a Carswell EL. Snapper ML. Hoveyda AH. Angew. Chem. Int. Ed. 2006; 45: 7230
9b Yanagisawa A. Arai T. Chem. Commun. 2008; 1165

10 Yuan Z.-L. Jiang J.-J. Shi M. Tetrahedron 2009; 65: 6001
11 Deng H.-P. Wei Y. Shi M. Adv. Synth. Catal. 2009; 351: 2897
12 Zheng L.-S. Li L. Yang K.-F. Zheng ZJ. Xiao X.-Q. Xu L.-W. Tetrahedron 2013; 69: 8777
13 Akiyama T. Honma Y. Itoh J. Fuchibe K. Adv. Synth. Catal. 2008; 350: 399

14a Hasegawa A. Naganawa Y. Fushimi M. Ishihara K. Yamamoto H. Org. Lett. 2006; 8: 3175
14b Liu H. Dagousset G. Masson G. Retailleau P. Zhu J. J. Am. Chem. Soc. 2009; 131: 4598
14c Zhou F. Yamamoto H. Angew. Chem. Int. Ed. 2016; 55: 8970
14d Zhou F. Yamamoto H. Org. Lett. 2016; 18: 4974

For chiral phosphoric acids and their derivatives, see:

15a Liang Y. Rowland EB. Rowland GB. Perman JA. Antilla JC. Chem. Commun. 2007; 4477
15b Akiyama T. Chem. Rev. 2007; 107: 5744
15c Terada M. Synthesis 2010; 1929
15d Parmar D. Sugiono E. Raja S. Rueping M. Chem. Rev. 2014; 114: 9047
15e Parmar D. Sugiono E. Raja S. Rueping M. Chem. Rev. 2017; 117: 10608

For chiral imidodiphosphoric acids, see:

16a Coric I. List B. Nature 2012; 483: 315
16b Liao S. Čorić I. Wang Q. List B. J. Am. Chem. Soc. 2012; 134: 10765
16c Chen Y.-Y. Jiang Y.-J. Fan Y.-S. Sha D. Wang Q. Zhang G. Zheng L. Zhang S. Tetrahedron: Asymmetry 2012; 23: 904
16d Kim JH. Čorić I. Vellalath S. List B. Angew. Chem. Int. Ed. 2013; 52: 4474
16e Wu K. Jiang Y.-J. Sha D. Zhang S. Chem. Eur. J. 2013; 19: 474
16f Jindal G. Sunoj RB. Angew. Chem. Int. Ed. 2014; 53: 4432
16g An D. Fan Y.-S. Gao Y. Zhu ZQ. Zheng LY. Zhang SQ. Eur. J. Org. Chem. 2014; 301
16h Zhuo M.-H. Jiang Y.-J. Fan Y.-S. Gao Y. Liu S. Zhang S. Org. Lett. 2014; 16: 1096
16i Liu L. Leutzsch M. Zheng Y. Alachraf MW. Thiel W. List B. J. Am. Chem. Soc. 2015; 137: 13268
16j An D. Zhu Z. Zhang G. Gao Y. Gao J. Han X. Zheng L. Zhang S. Tetrahedron: Asymmetry 2015; 26: 897
16k Wu K. Zhuo MH. Sha D. Fan Y.-S. An D. Jiang Y.-J. Zhang S. Chem. Commun. 2015; 51: 8054
16l Xie Y. Cheng G.-J. Lee S. Kaib PS. J. Thiel W. List B. J. Am. Chem. Soc. 2016; 138: 14538
16m Zhuo MH. Liu GF. Song SL. An D. Gao J. Zheng L. Zhang S. Adv. Synth. Catal. 2016; 358: 808
16n An D. Guan X. Guan R. Jin L. Zhang G. Zhang S. Chem. Commun. 2016; 52: 11211
16o Simón L. Paton RS. Org. Biomol. Chem. 2016; 14: 3031
16p Das S. Liu L. Zheng Y. Alachraf MW. Thiel W. De CK. List B. J. Am. Chem. Soc. 2016; 138: 9429
16q Langdon SM. Tetrahedron 2016; 72: 5247
16r Liu G. Zhuo M. An D. Zhang G. Qin X. Gao J. Fan S. Zhang S. Asian J. Org. Chem. 2017; 6: 807
16s Wang C. An D. Guan X. Fan Y. Liu G. Zhang G. Zhang S. Eur. J. Org. Chem. 2017; 1865
16t Tsuji N. Kennemur JL. Buyck T. Lee S. Prévost S. Kaib PS. J. Bykov D. Farès C. List B. Science 2018; 359: 1501

17 CCDC 1576505 (for 8t) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre: http://www.ccdc.cam.ac.uk/data_request/cif
18 General Procedure for the Asymmetric Vinylogous Mannich Reaction of Aldimines with 2-(Trimethylsilyloxy)furan A mixture of aldimine 6 (0.1 mmol), VAPOL imidodiphosphoric acid 4 (5 mol%) HP-β-CD (4 mg), toluene (1 mL) was stirred at –40 °C for 15 min. Then, 2-(trimethylsilyloxy)furan 7 (0.3 mmol) was added under an argon atmosphere at –40 °C. After the reaction was completed (monitored by TLC), the mixture was purified by silica gel chromatography (ethyl acetate/petroleum ether 1:6) to directly afford product 8. (S)-5-[(R)-Phenyl(phenylamino)methyl]furan-2(5H)-one (8a) Colorless oil, 97% yield, [α]_D ²⁰ = –124.2 (c = 1.5, CHCl₃), 80% ee, 93:7 dr [DaicelChiralcel OJ-H column, n-hexane/ethanol 80:20, 1.0 mL/min, λ = 254 nm, t(major) = 27.865 min, t(minor) = 32.746 min]. ¹H NMR (400 MHz, DMSO-d ₆): δ = 7.81 (d, J = 8.0 Hz, 1 H),7.43 (d, J = 4.0 Hz, 2 H), 7.30 (t, J = 8.0 Hz, 2 H), 7.24–7.21 (m, 1 H), 7.02 (t, J = 8.0 Hz, 2 H), 6.68 (d, J = 8.0 Hz, 2 H), 6.53 (t, J = 8.0 Hz, 1 H), 6.40 (d, J = 8.0 Hz, 1 H), 6.17–6.15 (m, 1 H), 5.50 (d, J = 4.0 Hz, 1 H), 4.90–4.87 (m, 1 H) ppm. ¹³C NMR (100 MHz, DMSO-d ₆): δ = 173.1, 156.5, 147.7, 138.8, 129.2, 128.4, 128.3, 127.9, 122.2, 117.0, 113.7, 85.5, 58.6 ppm. HRMS (ESI): m/z [M + H]⁺ calcd for C₁₇H₁₅NO₂: 266.1103; found: 266.1188.

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