Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2014; 25(2): 251-254
DOI: 10.1055/s-0033-1340163
DOI: 10.1055/s-0033-1340163
letter
A Chiral Benzyl Group as a Chiral Auxiliary and Protecting Group for the Synthesis of Optically Active 1,2-Diols and (+)-Frontalin
Further Information
Publication History
Received: 22 August 2013
Accepted after revision: 30 September 2013
Publication Date:
05 November 2013 (online)
Abstract
Chelation-controlled asymmetric nucleophilic addition of a Grignard reagent to chiral α-benzyloxy ketones gives the corresponding alcohols with high diastereoselectivities (up to 96% de) by 1,4-asymmetric induction. A chiral benzyl group is used as a chiral auxiliary as well as a protecting group for the synthesis of optically active 1,2-diols and (+)-frontalin.
Key words
nucleophilic addition - diols - α-benzyloxy ketones - (+)-frontalin - stereoselective synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Yildiz T, Yusufoglu A. Monatsh. Chem. 2013; 144: 183
- 2 Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994; 94: 2483
- 3a Han P, Wang R, Wang DZ. Tetrahedron 2011; 67: 8873
- 3b Vanhessche KP. M, Sharpless KB. J. Org. Chem. 1996; 61: 7978
- 4a Jung JE, Ho H, Kim H.-D. Tetrahedron Lett. 2000; 41: 1793
- 4b Rhee HJ, Beom HY, Kim H.-D. Tetrahedron Lett. 2004; 45: 8019
- 4c Lee H, Kim H, Yoon T, Kim B, Kim S, Kim H.-D, Kim D. J. Org. Chem. 2005; 70: 8723
- 5a Vargas-Diaz ME, Joseph-Nathan P, Tamariz J, Zepeda G. Org. Lett. 2007; 9: 13
- 5b Campagna M, Trzoss M, Bienz S. Org. Lett. 2007; 9: 3793
- 5c Trzoss M, Shao J, Bienz S. Tetrahedron 2002; 58: 5885
- 5d Charette AB, Mellon C, Motamedi M. Tetrahedron Lett. 1995; 36: 8561
- 5e Agami C, Couty F, Lequesne C. Tetrahedron 1995; 51: 4043
- 6 Chang M, Kim TH, Kim H.-D. Tetrahedron: Asymmetry 2008; 12: 1503
- 7 Sato F, Kobayashi Y, Takahashi O, Chiba T, Takeda Y, Kusakabe M. J. Chem. Soc., Chem. Commun. 1985; 1636
- 8 Schlenk W, Schlenk WJr. Chem. Ber. 1929; 62: 920
- 10a Fujisawa T, Watai T, Sugiyama T, Ukaji Y. Chem Lett. 1989; 18: 2045
- 10b Colombo L, Di Giacomo M, Brussotti G, Milano E. Tetrahedron Lett. 1995; 36: 2863
- 11 Chikashita H, Nikaya T, Uemura H, Itoh K. Bull. Chem. Soc. Jpn. 1989; 62: 2121
- 12a Nishimura Y, Mori K. Eur. J. Org. Chem. 1998; 233
- 12b Kouklovsky C, Dirat O, Berranger T, Langlois Y, Tran-Huu-Dau ME, Riche C. J. Org. Chem. 1998; 63: 5123
- 12c Yus M, Ramón DJ, Prieto O. Tetrahedron: Asymmetry 1998; 9: 2611
- 12d Bravo P, Frigerio M, Ono T, Panzeri W, Peseti C, Sekine A, Viani F. Eur. J. Org. Chem. 2000; 1387
- 12e Kanada RM, Taniguchi T, Ogasawara K. Tetrahedron Lett. 2000; 41: 3631
- 12f Yus M, Ramón DJ, Prieto O. Eur. J. Org. Chem. 2003; 2745
- 12g Yang X, Luo S, Hua C, Zhai H. Tetrahedron 2003; 59: 8551
- 12h Ortiz B, Sanchez-Obregon R, Toscano RA, Yuste F. Synthesis 2008; 2105
- 12i Singh S, Guiry PJ. Tetrahedron 2010; 66: 5701
- 13 Due to the small amount obtained and volatile nature of frontalin, we were unable to purify it in order to record an accurate reading of the optical rotation.
- 14 Ohrui H, Emoto S. Agric. Biol. Chem. 1976; 40: 2267
For some selected examples, see: