Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Perspective

Sparteine Family: Privileged Chiral Ligands in Transition Metal Catalysis

Author(s): Mingyu Zhang, Yuting Yan, Hexin Sun, Xuegang Fu* and Jianhui Huang*

Volume 26, Issue 5, 2022

Published on: 25 May, 2022

Page: [427 - 431] Pages: 5

DOI: 10.2174/1385272826666220408105613

Abstract

Chiral ligands are the footstones for asymmetric synthesis, constructing the enantioenriched molecules that are widely used in material and medicinal sciences. Naturally occurring compounds, such as proline analogues and cinchona alkaloids, are widely used as privileged ligands in asymmetric synthesis. Sparteine, a natural alkaloid firstly reported in 1968, was also employed in asymmetric synthesis, albeit with less satisfactory results. In this perspective, transition metal-involved asymmetric transformations using sparteine or family members as ligands are overviewed and discussed. The design and perspective of ligands with similar skeleton are also proposed.

Keywords: Sparteine, chiral ligand, asymmetric synthesis, green chemistry, transition metal catalysis, cinchona alkaloids.

Next »
Graphical Abstract
[1]
Villalpando-Vargas, F.; Medina-Ceja, L. Sparteine as an anticonvulsant drug: Evidence and possible mechanism of action. Seizure, 2016, 39, 49-55.
[http://dx.doi.org/10.1016/j.seizure.2016.05.010] [PMID: 27262285]
[2]
Nozaki, H.; Aratani, T.; Toraya, T.; Noyori, R. Asymmetric ring opening of gem-dibromocyclopropanes leading to allenic hydrocarbons. Tetrahedron Lett., 1968, 9(17), 2087-2090.
[http://dx.doi.org/10.1016/S0040-4039(00)89749-X]
[3]
Beak, P.; Kerrick, S.T. Asymmetric deprotonations: Enantioselective syn-theses of 2-substituted (tert-butoxycarbonyl)pyrrolidines. J. Am. Chem. Soc., 1991, 113(25), 9708-9710.
[http://dx.doi.org/10.1021/ja00025a066]
[4]
Hoppe, D.; Hintze, F.; Trhben, P. Chiral lithium-1-oxyalkanides by asym-metric deprotonation; enantioselective Synthesis of 2-hydroxyalkanoic ac-ids and secondary alkanols. Angew. Chem. Int. Ed. Engl., 1990, 29(12), 1422-1424.
[http://dx.doi.org/10.1002/anie.199014221]
[5]
O’Brien, P. Basic instinct: Design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis. Chem. Commun. (Camb.), 2008, (6), 655-667.
[http://dx.doi.org/10.1039/B711420F] [PMID: 18478687]
[6]
Campos, K.R.; Klapars, A.; Waldman, J.H.; Dormer, P.G.; Chen, C.Y. Enan-tioselective, palladium-catalyzed α-arylation of N-Boc-pyrrolidine. J. Am. Chem. Soc., 2006, 128(11), 3538-3539.
[http://dx.doi.org/10.1021/ja0605265] [PMID: 16536525]
[7]
Lin, W.; Zhang, K-F.; Baudoin, O. Regiodivergent enantioselective C-H functionalization of Boc-1,3-oxazinanes and application to the synthesis of β2 and β3-amino acids. Nat. Catal., 2019, 2(10), 882-888.
[http://dx.doi.org/10.1038/s41929-019-0336-1] [PMID: 31620675]
[8]
Burns, M.; Essafi, S.; Bame, J.R.; Bull, S.P.; Webster, M.P.; Balieu, S.; Dale, J.W.; Butts, C.P.; Harvey, J.N.; Aggarwal, V.K. Assembly-line synthesis of organic molecules with tailored shapes. Nature, 2014, 513(7517), 183-188.
[http://dx.doi.org/10.1038/nature13711] [PMID: 25209797]
[9]
Yoon, T.P.; Jacobsen, E.N. Privileged chiral catalysts. Science, 2003, 299(5613), 1691-1693.
[http://dx.doi.org/10.1126/science.1083622] [PMID: 12637734]
[10]
Guetté, M.; Capllon, J.; Guetté, J.P. Synthese asymetrique de β-hydroxyesters par reaction de Reformatsky en presence de (-)-sparteine. Tetrahedron, 1973, 29, 3659-3667.
[http://dx.doi.org/10.1016/S0040-4020(01)93530-6]
[11]
Trost, B.; Dietsche, T. New synthetic reactions. Allylic alkylations asym-metric induction in allylic alkylations. J. Am. Chem. Soc., 1973, 95(24), 8200-8201.
[http://dx.doi.org/10.1021/ja00805a056]
[12]
Maheswaran, H.; Joseph, P.J.A.; Prasanth, K.L.; Priyadarshini, S.; Satyana-rayana, P.; Likhar, P.R.; Kantam, M.L. Investigations of enantioreversal in both direct and directed enantioselective aldol reactions catalyzed by CuCl2[(-)-sparteine] and NiCl2[(-)-sparteine] complexes. Tetrahedron Asymmetry, 2010, 21(17), 2158-2166.
[http://dx.doi.org/10.1016/j.tetasy.2010.07.008]
[13]
Chopade, M.U. Enantioselective Michael addition of diethyl malonate on substituted chalcone catalysed by nickel-sparteine complex. Organic Chem. Curr. Res., 2017, 6(1)
[http://dx.doi.org/10.4172/2161-0401.1000178]
[14]
Maheswaran, H.; Prasanth, K.L.; Krishna, G.G.; Ravikumar, K.; Sridhar, B.; Kantam, M.L. Enantioselective nitroaldol (Henry) reaction using copper(II) complexes of (-)-sparteine. Chem. Commun. (Camb.), 2006, (39), 4066-4068.
[http://dx.doi.org/10.1039/B610203D] [PMID: 17024250]
[15]
Kiyooka, S.; Takeshita, Y.; Tanaka, Y.; Higaki, T.; Wada, Y. Dicationic ((-)-sparteine)palladium-catalyzed enantioselective aldol reaction of aldehydes with 1-phenyl-1-trimethylsilyloxyethene, proceeding via a palladium eno-late. Tetrahedron Lett., 2006, 47(26), 4453-4456.
[http://dx.doi.org/10.1016/j.tetlet.2006.04.068]
[16]
Smrcina, M.; Poláková, J.; Vyskocil, S.; Kocovský, P. Synthesis of enanti-omerically pure binaphthyl derivatives. Mechanism of the enantioselective, oxidative coupling of naphthols and designing a catalytic cycle. J. Org. Chem., 1993, 58(17), 4534-4538.
[http://dx.doi.org/10.1021/jo00069a010]
[17]
Trend, R.M.; Ramtohul, Y.K.; Ferreira, E.M.; Stoltz, B.M. Palladium-catalyzed oxidative wacker cyclizations in nonpolar organic solvents with molecular oxygen: A stepping stone to asymmetric aerobic cyclizations. Angew. Chem. Int. Ed., 2003, 42(25), 2892-2895.
[http://dx.doi.org/10.1002/anie.200351196] [PMID: 12833351]
[18]
Yip, K.T.; Yang, M.; Law, K.L.; Zhu, N.Y.; Yang, D. Pd(II)-catalyzed enan-tioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation. J. Am. Chem. Soc., 2006, 128(10), 3130-3131.
[http://dx.doi.org/10.1021/ja060291x] [PMID: 16522078]
[19]
Togni, A. Asymmetric allylic alkylation catalyzed by palladium-sparteine complexes. Tetrahedron Asymmetry, 1991, 2(7), 683-690.
[http://dx.doi.org/10.1016/S0957-4166(00)86122-4]
[20]
Kang, J. Cho, W.O.; Cho, H.G. (-)-α-isosparteine as a chiral ligand in asymmetric allylic alkylation. Tetrahedron Asymmetry, 1994, 5(7), 1347-1352.
[http://dx.doi.org/10.1016/0957-4166(94)80176-2]
[21]
Jensen, D.R.; Pugsley, J.S.; Sigman, M.S. Palladium-catalyzed enantioselec-tive oxidations of alcohols using molecular oxygen. J. Am. Chem. Soc., 2001, 123(30), 7475-7476.
[http://dx.doi.org/10.1021/ja015827n] [PMID: 11472200]
[22]
Ferreira, E.M.; Stoltz, B.M. The palladium-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen. J. Am. Chem. Soc., 2001, 123(31), 7725-7726.
[http://dx.doi.org/10.1021/ja015791z] [PMID: 11481006]
[23]
Germain, A.R.; Bruggemeyer, D.M.; Zhu, J.; Genet, C.; O’Brien, P.; Porco, J.A. Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization. J. Org. Chem., 2011, 76(8), 2577-2584.
[http://dx.doi.org/10.1021/jo102448n] [PMID: 21401026]
[24]
Nakamura, D.; Kakiuchi, K.; Koga, K.; Shirai, R. Design and synthesis of novel C2-symmetric chiral piperazines and an application to asymmetric ac-ylation of σ-symmetric 1,2-diols. Org. Lett., 2006, 8(26), 6139-6142.
[http://dx.doi.org/10.1021/ol0626387] [PMID: 17165949]
[25]
Goldberg, Y.; Alper, H. Asymmetric hydrosilylation of prochiral ketones catalyzed by Rh(I) complexes and (-)-sparteine. Tetrahedron Asymmetry, 1992, 3(8), 1055-1062.
[http://dx.doi.org/10.1016/S0957-4166(00)86039-5]
[26]
Canipa, S.J.; Stute, A.; O’Brien, P. Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Compar-ison of (-)-sparteine and (+)-sparteine surrogates. Tetrahedron, 2014, 70(40), 7395-7403.
[http://dx.doi.org/10.1016/j.tet.2014.06.117]
[27]
Scharnagel, D.; Müller, A.; Prause, F.; Eck, M.; Goller, J.; Milius, W.; Breun-ing, M. The first modular route to core-chiral bispidine ligands and their ap-plication in enantioselective copper(II)-catalyzed Henry reactions. Chemistry, 2015, 21(35), 12488-12500.
[http://dx.doi.org/10.1002/chem.201502090] [PMID: 26230668]
[28]
Ebner, D.C.; Trend, R.M.; Genet, C.; McGrath, M.J.; O’Brien, P.; Stoltz, B.M. Angew. Chem. Int. Ed., 2008, 47, 6367-6370.
[http://dx.doi.org/10.1002/anie.200801865]
[29]
Zeng, F.; Chen, C.; Liu, L.; Li, Y.; Li, B.; Lin, G.; Huang, S.; Zhang, M.; Yan, Y.; Zhang, Y.; Dang, Y.; Huang, J. Untethering sparteine: 1,3-diamine ligand for asymmetric synthesis in water. ChemRxivCambridge Open Engage, 2021.
[http://dx.doi.org/10.26434/chemrxiv-2021-tlgj2-v3]

© 2024 Bentham Science Publishers | Privacy Policy