, Chem. Soc. Rev, vol.34, p.677, 2005.
117, 6249, and references therein; b) K. A. Muraglia, J. Am. Chem. Soc, 1995. ,
, Nature, vol.567, p.405, 2019.
, J. Am. Chem. Soc, vol.134, p.17919, 2012.
, In the cyclic series where strong organizational bias exists, several polyols based notably on catechols, or rigid tripodal cyclohexanes have been developed, see: a), Org. Biomol. Chem, vol.1, p.3874, 2003.
, Tetrahedron Lett, p.51, 2010.
, J. Org. Chem, p.1130, 2015.
, J. Am. Chem. Soc, vol.120, p.5389, 1661.
, Angew. Chem. Int. Ed, vol.424, p.7727, 2003.
2 1998, 2585; b), For notable examples of organogels notably based on 1,2-diols scaffolds, vol.7, p.7861, 2000. ,
, Angew. Chem. Int. Ed, vol.50, p.13, 1980.
, Angew. Chem. Int. Ed, vol.48, p.9533, 2012.
, Mar. Drugs, vol.13, p.206, 2010.
For another example of chlorinated bioisostere synthesis, see: d), Angew. Chem. Int. Ed, vol.131, p.4049, 2009. ,
, , p.4117, 2016.
, Chem. Soc. Rev, vol.317, p.320, 1881.
, Chem. Soc. Rev, vol.37, p.8315, 2008.
After the initial submission of this manuscript, Angew. Chem. Int. Ed, vol.50, 1701. ,
, Angew. Chem. Int. Ed, vol.58, 2019.
, , p.11106, 2019.
, For examples in drug design, vol.76, p.5291, 1455.
, Angew. Chem. Int. Ed, vol.51, p.2811, 2012.
20, 5274; c) A. Ricucci, J. Rodriguez, A. Quintard, Eur. J. Org. Chem, vol.7, p.580, 2017. ,
, This results in the possible formation of multiple stereoisomers. From the crude reaction mixture, it is difficult to determine the exact dr and ee of the reaction, but according to 19 F NMR spectroscopy the desired adducts are formed with about 80 % of the major diastereomer, These molecules have four acyclic stereogenic centers created in distinct steps
Alternatively, nonhalogenated 1,3,5-triols could also be accessed by a reductive coupling we recently developed: b) A. Quintard, Org. Biomol. Chem, vol.11, p.453, 2013. ,
, CCDC 1879983, 1879890, and 1879889 contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre
95, 1609; b), For studies related to fluorohydrin conformations, 1991. ,
, Org. Biomol. Chem, vol.2, p.732, 2004.
, Synthesis, vol.47, p.306, 2015.
27, 309; b) A. Gavezzotti, G. Filippini, Acc. Chem. Res, p.4831, 1994. ,
, See the Supporting Information for details
, Theor. Chem. Acc, vol.120, p.215, 2008.
, Gaussian 09, Revision A.1, 2009.
, , 2013.
, For reviews, vol.47, p.8122, 2008.
1, 437; c) B. Escuder, F. Rodriguez-Llansola, J. F. Miravet, New J. Chem, vol.34, 1044. ,
, Chem. Soc. Rev, 2011.
, Chem. Soc. Rev, vol.41, 2012.
, Chem. Soc. Rev, vol.45, p.712, 2016.
, Chem. Eur. J, vol.11, p.6552, 2005.
37, 2699; c), Angew. Chem. Int. Ed, vol.54, 2008. ,
, Org. Chem. Front, vol.127, p.2885, 2015.
For a recent review, Chem. Rev, vol.115, p.8038, 2015. ,
, Chem. Soc. Rev, vol.40, p.12792, 1305.
, Unfortunately, in the case of chlorohydrin 8 g, anion binding could not be determined accurately due to lower stability
, We also confirmed this catalyst geometry by DFT calculations; see the Supporting Information for details
, Angew. Chem. Int. Ed, vol.44, p.6576, 2005.
, On diluting the reaction mixture by a factor of two, the same increase in the reaction rate was observed with fluorinated triol, 2019.
, Accepted manuscript online, 2019.
, Version of record online, 2019.
, Chem. Eur. J, vol.25, pp.15098-15105, 2019.