Citation: Ji Hong-Tao, Tian Qing-Shan, Xiang Jian-Nan, Zhang Guo-Zhu. Chromium-catalyzed asymmetric synthesis of 1, 3-diols[J]. Chinese Chemical Letters, ;2017, 28(6): 1182-1184. doi: 10.1016/j.cclet.2017.03.016 shu

Chromium-catalyzed asymmetric synthesis of 1, 3-diols

a.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Corresponding author: Xiang Jian-Nan, jnxiang@hnu.edu.cn Zhang Guo-Zhu, guozhuzhang@sioc.ac.cn
Received Date: 18 January 2017
Revised Date: 8 March 2017
Accepted Date: 9 March 2017
Available Online: 12 June 2017

Figures(3)

An efficient, chromium-catalyzed highly enantioselective preparation of protected 1, 3-diols has been achieved. In the presence of a chiral chromium catalyst using the carbazole-based bisoxazoline as the chiral ligand, a variety of optically pure 1, 3-diols were synthesized in 34%-87% yields with up to 98% ee. The benzyl as well as silyl ethers were suitable substitutions for the hydroxyl group. Meanwhile, aromatic, aliphatic and α, β-unsaturated aldehydes are well tolerated under the mild reaction conditions.
- 1, 3-Diol,
- Asymmetric,
- Chromium-catalyzed,
- Allylation,
- Bisoxazoline
1. [1]
  (a) Y. Zhou, P. Prediger, L.C. Dias, A.C. Murphy, F. Leadlay, Macrodiolide formation by the thioesterase of a modular polyketide synthase, Angew. Chem. Int. Ed. 54(2015) 5232-5324;
  (b) J.J. Feng, J. Victory, J. Garza, M.J. Krische, Redox-triggered C-C coupling of alcohols and vinyl epoxides:diastereo-and enantioselective formation of allcarbon quaternary centers via tert-(hydroxy)-prenylation, J. Am. Chem. Soc. 136(2014) 8911-8914;
  (c) C. Daniel, R. Schmitt, A. Marie, D. Schmitt, M.J. Krische, Iridium-catalyzed allylation of chiral-stereogenic alcohols:bypassing discrete formation of epimerizable aldehyde, Org. Lett. 14(2012) 6302-6305;
  (d) L.M. Geary, M.J. Krische, Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons:ruthenium catalyzed[4+2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels, J. Am. Chem. Soc. 135(2013) 3796-3799.
2. [2]
  Pérez M., del Pozo C., Reyes F.. Total synthesis of natural myriaporones[J]. Angew. Chem. Int. Ed., 2004,43:1724-1727. doi: 10.1002/(ISSN)1521-3773
3. [3]
  Taylor R.E., Fleming K.N.. Total synthesis and stereochemical assignment of myriaporones 13. and 4[J]. Angew. Chem. Int. Ed., 2004,43:1728-1730. doi: 10.1002/(ISSN)1521-3773
4. [4]
  Ehrlich G., Hassfeld J., Eggert U., Kalesse M.. The total synthesis of (+)-tedanolide[J]. J. Am. Chem. Soc., 2006,128:14038-14039. doi: 10.1021/ja0659572
5. [5]
  Smith Ⅲ A.B., Lee D.. Total synthesis of (+)-tedanolide[J]. J. Am. Chem. Soc., 2007,129:10957-10962. doi: 10.1021/ja073329u
6. [6]
  Abdul Muhit M., Noguchi H.. Phenolic constituents of the bangladeshi medicinal plant pothos scandens and their anti-estrogenic, hyaluronidase inhibition, and histamine release inhibitory activities[J]. Phytochemistry, 2016,121:30-37. doi: 10.1016/j.phytochem.2015.10.009
7. [7]
  Knapp H., Winterhalter P.J.. Agric (s)-3.7-dimethyl-5-octene-1, 7-diol and related oxygenated monoterpenoids from petals of rosa damascena mill[J]. Food Chem., 1998,46:1966-1970. doi: 10.1021/jf970987x
8. [8]
  Andre L.B., Barreiros S., David J.M.. A-type proanthocyanidin antioxidant from dioclea lasiophyll[J]. Phytochmistry, 2000,55:805-808. doi: 10.1016/S0031-9422(00)00297-1
9. [9]
  Matsuda H., Yoshikawa M.. Inhibitors from the rhizomes of alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity[J]. Bioorg. Med. Chem., 2006,14:138-142. doi: 10.1016/j.bmc.2005.08.003
10. [10]
  Rukachaisirikul V., Sakayaroj J.. Rare 2-phenylpyran-4-ones from these agrassderivedfungipolyporales PSU-ES44 and PSU-ES83[J]. Tetrahedron, 2013,69:6981-6986. doi: 10.1016/j.tet.2013.06.059
11. [11]
  Esmurziev A., Sunby E., Hoff B.H.. Regioselective c-6 hydrolysis of methylobenzoyl-pyranosides catalysed by candida rugosa lipase[J]. Eur. J. Org. Chem, 2009:1592-1597.
12. [12]
  (a) Y. Masuyama, J.P. Takahara, Y. Kurusu, Allylic alcohols as synthons of allylic carbanions, palladium-catalyzed carbonyl allylation by allylic alcohols with tin dichloride, J. Am. Chem. Soc. 110(1988) 4473-4474;
  (b) J.P. Takahara, Y. Masuyama, Y. Kurusu, Palladium-catalyzed carbonyl allylation by allylic alcohols with stannous chloride, J. Am. Chem. Soc. 114(1992) 2577-2586;
  (c) X.L. Wang, Y.Y. Yang, H.J. Chen, Y. Wu, D.S. Ma, Synthesis of vinylchorinecontaining 1, 3-diols from marine cyanophyte, Tetrahedron 70(2014) 4571-4579;
  (d) S. Araki, K. Kameda, J. Tanaka, et al., Umpolung of vinyloxiranes:regio-and stereoselectivity of the In/Pd-mediated allylation of carbonyl compounds, J. Org. Chem. 66(2001) 7919-7921;
  (e) M. Gagliardo, N. Selander, N.C. Mehendale, et al., Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes:synthesis and tandem catalytic activity of the first PCS-pincer palladium complex, Chem. Eur. J. 14(2008) 4800-4809.
13. [13]
  Bandini M., Cozzi G., Licciulli S. A.. Umani-Ronchi. A cross metathesis based protocol for the effective synthesis of functionalised allyl bromides and chlorides[J]. Synthesis, 2004,3:409-414.
14. [14]
  Lombardo M., Licciulli S., Morganti S., Trombini C.. Trombini C.. 3-Chloropropenyl pivaloate in organic synthesis:the first asymmetric catalytic entry to syn-alk-1-ene-3. 4-diols[J]. Chem. Comm, 20031762.
15. [15]
  (a) W. Chen, Q. Yang, T. Zhou, Q. Tian, G. Zhang, Enantioselective synthesis of α-exo-methyleneg-butyrolactones via chromium catalysis, Org. Lett.17(2015) 5236-5239;
  (b) Q. Tian, G. Zhang, Recent advances in the asymmetric Nozaki-Hiyama-Kishi reaction, Synthesis 48(2016) 4048-4049.
16. [16]
  Tian Q., Bai B., Chen B., Zhang G.. Chromium-catalyzed asymmetric dearomatization addition reactions of halomethyl heteroarenes[J]. Org. Lett., 2016,18:1828-1831. doi: 10.1021/acs.orglett.6b00559
17. [17]
  Xiong Y., Zhang G.. Enantioselective synthesis of quaternary stereocenters via chromium catalysis[J]. Org. Lett., 2016,18:5094-5097. doi: 10.1021/acs.orglett.6b02540
18. [18]
  (a) G.C. Hargaden, P.J. Guiry, The development of the asymmetric NozakiHiyama-Kishi reaction, Adv. Synth. Catal. 349(2007) 2407;
  (b) K. Sugimoto, S. Aoyagi, C. Kibayashi, Enantioselective allylation of aldehydes with (dialkoxyallyl) chromium(Ⅲ) complexes, J. Org. Chem. 62(1997) 2322-2323;
  (c) M. Bandini, P.G. Cozzi, P. Melchiorre, A. Umani-Ronchi, The first catalytic enantioselective nozaki-hiyama reaction, Angew. Chem. Int. Ed. 38(1999) 3357-3359;
  (d) A. Berkessel, D. Menche, C.A. Sklorz, M. Schroöder, I. Paterson, A highly enantioselective catalyst for the asymmetric nozaki-hiyama-kishi reaction of allylic and vinylic halides, Angew. Chem. Int. Ed. 42(2003) 1062-1065;
  (e) C. Chen, K. Tagami, Y. Kishi, Ni(Ⅱ)/Cr(Ⅱ)-mediated coupling reaction:an asymmetric process, J. Org. Chem. 60(1995) 5386-5387;
  (f) H.W. Choi, D. Demeke, F.A. Kang, et al., Synthetic studies on the marine natural product halichondrins, Pure Appl. Chem. 75(2003) 1-17;
  (g) H.B. Guo, C.G. Dong, D.S. Kim, et al., Toolbox approach to the search for effective ligands for catalytic asymmetric Cr-mediated coupling reactions, J. Am. Chem. Soc. 131(2009) 15387-15393.
19. [19]
  (a) Y. Okude, S. Hirano, T. Hiyama, H. Nozaki, Grignard-type carbonyl addition of allyl halides by means of chromous salt. A chemospecific synthesis of homoallyl alcohols, J. Am. Chem. Soc. 99(1977) 3179-3181;
  (b) K. Takai, K. Kimura, T. Kuroda, T. Hiyama, H. Nozaki, Selective grignard-type carbonyl addition of alkenyl halides mediated by chromium (Ⅱ) chloride, Tetrahedron Lett. 24(1983) 5281-5284;
  (c) H. Jin, J.I. Uenishi, W.J. Christ, Y. Kishi, Catalytic effect of nickel(Ⅱ) chloride and palladium(Ⅱ) acetate on chromium(Ⅱ)-mediated coupling reaction of iodo olefins with aldehydes, J. Am. Chem. Soc. 108(1986) 5644-5646;
  (d) K. Takai, M. Tagashira, T. Kuroda, et al., Reactions of alkenylchromium reagents prepared from alkenyl trifluoro-methanesulfonates (triflates) with chromium(Ⅱ) chloride under nickel catalysis, J. Am. Chem. Soc. 108(1986) 6048-6050;
  (e) M. Avalos, R. Babiano, P. Cintas, J.L. Jimenez, J.C. ' Palacios, Synthetic variations based on low-valent chromium:new developments, Chem. Soc. Rev. 28(1999) 169-177.
20. [20]
  (a) M. Inoue, T. Suzuki, M. Nakada, A new asymmetric tridentate carbazole ligand:its preparation and application to Nozaki-Hiyama allylation, Synlett 4(2003) 570-572;
  (b) M. Inoue, T. Suzuki, M. Nakada, Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis (oxazolinyl) carbazole ligand, J. Am. Chem. Soc. 125(2003) 1140-1141.
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