OALib Journal期刊
ISSN: 2333-9721
费用：99美元

投递稿件

查看量	下载量

相关文章
更多...

化学学报 2014

手性膦烯配体在铑催化的芳基硼酸对β-芳基-α,β-不饱和磺酸酯不对称共轭加成反应中的应用

DOI: 10.6023/A14060436, PP. 815-819

于月娜,徐明华

Keywords: 不对称催化,膦烯配体,α,β-不饱和磺酸酯,1,4-加成,手性偕二芳基化合物

Full-Text Cite this paper Add to My Lib

Abstract:

报道了手性膦烯配体在金属铑催化的芳基硼酸对β-芳基-α，β-不饱和磺酸酯不对称共轭加成中的应用.经过系统的反应条件筛选和配体结构优化，发现含手性1，1'-联-2-萘酚骨架的膦烯配体L7与Rh（I）形成的催化剂可以高对映选择性地实现β-芳基-α，β-不饱和磺酸酯化合物的不对称1，4-加成反应.此反应体系条件温和，底物普适性广，并取得了较高的收率（upto95%）和优秀的对映选择性（upto99%ee），为合成手性偕二芳基取代的磺酸酯类化合物提供了一种新方法.

References

[1]	(e) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 67, 3221.
[2]	(f) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
[3]	(g) Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 5560.
[4]	(h) López, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179.
[5]	(i) López, F.; Minnaard, A. J.; Feringa, B. L. In The Chemistry of Organomagnesium Compounds, Eds.: Rappoport, Z.; Marek, I., Wiley, Chichester, U. K., 2008; Part 2, Chapter 17.
[6]	(j) Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
[7]	For reviews, see: (a) Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95.
[8]	(b) Partyka, D. V. Chem. Rev. 2011, 111, 1529.
[9]	(c) Berthon, G.; Hayashi, T. In Catalytic Asymmetric Conjugate Reactions, Ed.: Córdova, A., Wiley-VCH, Weinheim, Germany, 2010, Chapter 1, p. 1.
[10]	(d) Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39, 2093.
[11]	(e) Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840.
[12]	(f) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313.
[13]	(g) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
[14]	(h) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
[15]	(i) Bolm, C.; Hildebrand, J. P.; Mu？iz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
[16]	(j) Christoffers, J.; Koripelly, G.; Rosiak, A.; R？ssle, M. Synthesis 2007, 1279.
[17]	(k) Enders, D.; Lüttgen, K.; Narine, A. A. Synthesis 2007, 959.
[18]	(l) Hayashi, T. Synlett 2001, 879.
[19]	(m) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
[20]	(n) Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240.
[21]	Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
[22]	Early studies of α,β-unsaturated ketones, see: (a) Reetz, M. T.; Moulin, D.; Gosberb, A. Org. Lett. 2001, 3, 4083.
[23]	(b) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932.
[24]	(c) Boiteau, J. G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681.
[25]	(d) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 1040.
[26]	(e) Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
[27]	α,β-Unsaturated Esters, Amides, and Aldehydes: (a) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
[28]	(b) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
[29]	(c) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
[30]	(d) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
[31]	(e) Paquin, J.-F.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850.
[32]	Alkenylphosphonates: Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591.
[33]	Nitroalkenes: Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
[34]	Alkenylheteroarenes and alkenylarenes: (a) Pattison, G.; Piraux, G.; Lam, H. W. J. Am. Chem. Soc. 2010, 132, 14373.
[35]	(b) Saxena, A.; Lam, H. W. Chem. Sci. 2011, 2, 2326.
[36]	For reviews, see: (a) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
[37]	(b) Rayner, C. M. Contemp. Org. Synth. 1996, 3, 499.
[38]	(c) Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
[39]	(d) Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
[40]	(a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis;Tetrahedron Organic Chemistry Series 9, Pergamon Press, Oxford, U. K., 1992.
[41]	(b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
[42]	(c) Zhang, Z.; Xie, F.; Yang, B.; Yu, H.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 429. (张振锋, 谢芳, 杨波, 余焓, 张万斌, 有机化学, 2011, 31, 429.)
[43]	(d) Ying, A.; Wu, C.; Fu, Y.; Ren, S.; Liang, H. Chin. J. Org. Chem. 2012, 32, 1587. (应安国, 武承林, 付永前, 任世斌, 梁华定, 有机化学, 2012, 32, 1587.)
[44]	For reviews, see: (a) Tomioka, K.; Nagaoka, Y. Comprehensive Asymmetric Catalysis, Eds.: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer, New York, 1999, p. 1105
[45]	(b) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
[46]	(c) Krause, N.; Hoffmann-R？der, A. Synthesis 2001, 2, 171.
[47]	(d) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry, Ed.: Krause, N., VCH, Weinheim, Germany, 2002, p. 224.
[48]	(e) B？ckvall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291.
[49]	(f) Meadows, D. C.; Gervay-Hague, J. Med. Res. Rev. 2006, 26, 793.
[50]	(j) Tozer, M. J.; Harper, E. A.; Kalindjian, S. B.; Pether, M. J.; Shankley, N. P.; Watt, G. F. Bioorg. Med. Chem. Lett. 1999, 9, 1825.
[51]	(h) Tamamura, H.; Koh, Y.; Ueda, S.; Sasaki, Y.; Yamasaki, T.; Aoki, M.; Maeda, K.; Watai, Y.; Arikuni, H.; Otaka, A.; Mitsuya, H.; Fujii, N. J. Med. Chem. 2003, 46, 1764.
[52]	(i) Hanessian, S.; Sailes, H.; Therrien, E. Tetrahedron 2003, 59, 7047.
[53]	(j) Zajac, M.; Peters, R. Chem. Eur. J. 2009, 15, 8204.
[54]	For recent examples, see: (a) Enders, D.; Müller, S. F.; Raabe, G. Angew. Chem., Int. Ed. 1999, 38, 195.
[55]	(b) Grimaud, L.; Rotulo, D.; Ros-Perez, R.; Guitry-Azam, L.; Prunet, J. Tetrahedron Lett. 2002, 43, 7477.
[56]	(c) Luis, L. A.; Krische, M. J. Synthesis 2004, 2579.
[57]	(d) Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2010, 49, 8938.
[58]	(e) García Ruano, J. L.; Sch？pping, C.; Alvarado, C.; Alemán, J. Chem. Eur. J. 2010, 16, 8968.
[59]	(f) So, C. M.; Kume, S.; Hayashi, T. J. Am. Chem. Soc. 2013, 135, 10990.
[60]	(g) Lu, J.; Ye, J.; Duan, W. Chem. Commun. 2014, 50, 698.
[61]	For examples of copper-catalyzed asymmetric transformations, see: (a) Llamas, T.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2007, 46, 3329.
[62]	(b) Desrosiers, J.-N.; Charette, A. B. Angew. Chem., Int. Ed. 2007, 46, 5955.
[63]	(c) Bechara, W. S.; Charette, A. B. Org. Lett. 2008, 10, 2315.
[64]	(d) Bos, P. H.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2008, 10, 4219.
[65]	(e) Bos, P. H.; Maciá, B.; Fernández-Ibá？ez, M.á.; Minnaard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2010, 8, 47.
[66]	For a review of organocatalytic asymmetric addition to alkenyl sulfones, see: Nielsen, M.; Jacobsen, C. B.; Holub, N.; Paix？o, M. W.; J？rgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 2668.
[67]	(a) Mauleón, P.; Carretero, J. C. Org. Lett. 2004, 6, 3195.
[68]	(b) Mauleón, P.; Carretero, J. C. Chem. Commun. 2005, 41, 4961.
[69]	(c) Mauleón, P.; Alonso, I.; Rivero, M. R.; Carretero, J. C. J. Org. Chem. 2007, 72, 9924.
[70]	Nishimura, T.; Takiguchi, Y.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 9086.
[71]	(a) Jin, S.-S.; Wang, H.; Xu, M.-H. Chem. Commun. 2011, 47, 7230.
[72]	(b) Qi, W.-Y.; Zhu, T.-S.; Xu, M.-H. Org. Lett. 2011, 13, 3410.
[73]	(c) Jin, S.-S.; Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 1764.
[74]	(d) Zhu, T.-S.; Jin, S.-S.; Xu, M.-H. Angew. Chem., Int. Ed. 2012, 51, 780.
[75]	(e) Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 9158.
[76]	(f) Zhu, T.-S.; Chen, J.-P.; Xu, M.-H. Chem. Eur. J. 2013, 19, 865.
[77]	(g) Wang, H.; Jiang, T.; Xu, M.-H. J. Am. Chem. Soc. 2013, 135, 971.
[78]	(h) Wang, H.; Xu, M.-H. Synthesis 2013, 45, 2125.
[79]	(i) Li, Y.; Zhu, D.-X.; Xu, M.-H. Chem. Commun. 2013, 49, 11659.
[80]	(j) Li, Y.; Xu, M.-H. Chem. Commun. 2014, 50, 3771.
[81]	Yu, Y.-N.; Xu, M.-H. Org. Chem. Front. 2014, DOI: 10. 1039/c4qo00135d.
[82]	Selected early examples of the use of chiral phosphorus-based olefin ligands: (a) Maire, P.; Deblon, S.; Breher, F.; Geier, J.; B？hler, C.; Rügger, H.; Sch？nberg, H.; Grtrümacher, H. Chem. Eur. J. 2004, 10, 4198.
[83]	(b) Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Grützmacher, T. Angew. Chem., Int. Ed. 2005, 44, 4611.
[84]	(c) Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem. Int. Ed. 2007, 46, 3139.
[85]	(d) Mariz, R.; Brice？o, A.; Dorta, R.; Dorta, R. Organometallics 2008, 27, 6605.
[86]	(e) Liu, Z.; Du, H. Org. Lett. 2010, 12, 3054.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133