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Synlett 2016; 27(02): 173-176
DOI: 10.1055/s-0035-1560494
DOI: 10.1055/s-0035-1560494
synpacts
Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer
Further Information
Publication History
Received: 26 August 2015
Accepted after revision: 16 September 2015
Publication Date:
15 October 2015 (online)
Abstract
A brief overview of the development of direct substitution of the hydroxyl (OH) group of alcohols in our research group is presented. By applying a Brønsted acid, an intramolecular substitution of the OH group in stereogenic alcohols with chirality transfer was achieved. Noteworthy, the intramolecular substitution has a wide scope in respect to both the nucleophile and also the nucleofuge. A mechanistic study by both experiments and DFT calculations revealed a unique reaction pathway in which the Brønsted acid operates in a bifunctional manner to promote an SN2-type reaction mechanism.
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References
- 1a Mayr H, Kempf B, Ofial AR. Acc. Chem. Res. 2003; 36: 66
- 1b Emer E, Riccardo S, Capdevila MG, Petruzziello D, Vincentiis FD, Cozzi PG. Eur. J. Org. Chem. 2011; 647
- 1c Tamaru Y. Eur. J. Org. Chem. 2005; 2647
- 1d Muzart J. Eur. J. Org. Chem. 2007; 3077
- 1e Muzart J. Tetrahedron 2005; 61: 4179
- 1f Biswas S, Samec JS. M. Chem. Asian J. 2013; 8: 974
- 2 Anastas PT, Warner JC. Green Chemistry: Theory and Practice . Oxford University Press; USA: 2000
- 3a Krische M. Angew. Chem. Int. Ed. 2009; 48: 34
- 3b Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2011; 50: 4760
- 3c Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
- 3d Guillena G, Ramon DJ, Yus M. Chem. Rev. 2010; 110: 1611
- 4a Galkin MV, Sawadjoon S, Rohde V, Dawange M, Samec JS. M. ChemCatChem 2014; 6: 179
- 4b Galkin MV, Samec JS. M. ChemSusChem 2014; 7: 2154
- 4c Dawange M, Galkin MV, Samec JS. M. ChemCatChem 2015; 7: 401
- 4d Galkin MV, Dahlstrand C, Samec JS. M. ChemSusChem 2015; 8: 2142
- 4e Sawadjoon S, Lundstedt A, Samec JS. M. ACS Catal. 2013; 3: 635
- 5a Sawadjoon S, Sjöberg PJ. R, Orthaber A, Matsson O, Samec JS. M. Chem. Eur. J. 2014; 20: 1520
- 5b Sawadjoon S, Sjöberg PJ. R, Samec JS. M. Organometallics 2014; 33: 249
- 6 Kawai N, Jean-Marie L, Ohmi M, Uenishi J. J. Org. Chem. 2006; 71: 4530
- 7a Aponick A, Biannic B. Org. Lett. 2011; 13: 1330
- 7b Ghebreghiorgis T, Biannic B, Kirk BH, Aponick A, Ess DH. J. Org. Chem. 2013; 78: 7664
- 7c Aponick A, Li C.-Y, Biannic B. Org. Lett. 2008; 10: 669
- 7d Biannic B, Aponick A. Eur. J. Org. Chem. 2011; 6605
- 7e Paioiti PH, Aponick PH. Top. Curr. Chem. 2015; 357: 63
- 8a Mukherjee P, Widenhoefer RA. Chem. Eur. J. 2013; 19: 3437
-
8b Mukherjee P, Widenhoefer RA. Org. Lett. 2011; 13: 1334
- 8c Mukherjee P, Widenhoefer RA. Org. Lett. 2010; 12: 1184
- 9 Ghebreghiorgis T, Biannic B, Kirk BH, Ess DH, Aponick A. J. Am. Chem. Soc. 2012; 134: 16307
- 10 Bunrit A, Dahlstrand C, Olsson SK, Srifa P, Huang G, Orthaber A, Sjörberg P, Biswas S, Himo F, Samec JS. M. J. Am. Chem. Soc. 2015; 137: 4646
- 11a Simón L, Goodman JM. J. Am. Chem. Soc. 2008; 130: 8741
- 11b Marcelli T, Hammar P, Himo F. Chem. Eur. J. 2008; 14: 8562
- 11c Yamanaka M, Itoh J, Fuchibe K, Akiyama T. J. Am. Chem. Soc. 2007; 129: 6756
- 11d Simón L, Goodman JM. J. Am. Chem. Soc. 2009; 131: 4070
- 11e Chen D.-F, Han Z.-Y, Zhou X.-L, Gong L.-Z. Acc. Chem. Res. 2014; 47: 2365
- 11f Reuping M, Kuenkel A, Atodiresei I. Chem. Soc. Rev. 2011; 40: 4539