Helvetica Chimica Acta p. 2342 - 2349 (1985)
Update date:2022-08-11
Topics:
Seebach, Dieter
Renaud, Philippe
The coupling of chiral, non-racemic R* groups by Kolbe electrolysis of carboxylic acids R*COOH is used to prepare compounds with a 1,4- and 1,5-distance of the functional groups.The suitably protected β-hydroxycarboxylic acids (R)- or (S)-3-hydroxybutyric acid, (R)-4,4,4-trifluoro-3-hydroxybutyric acid (as acetates; see 1-6), and (S)-malic acid (as (2S,5S)-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-acetic acid, see 7) are decarboxylatively dimerized or "codimerized" with 2-methylpropanoic acid, with 4-(formylamino)butyric acid, and with monomethyl malonate and succinate.The products formed are derivatives of (R,R)-1,1,1,6,6,6-hexafluoro-2,5-hexanediol (see 8), of (R)-5,5,5-trifluoro-4-hydroxypentanoic acid (see 9, 10), of (R)- and (S)-5-hydroxyhexanoic acid (see 11) and its trifluoro analogue (see 12, 13), of (S)-2-hydroxy- and (S,S)-2,5-dihydroxyadipic acid (see 23, 20), of (S)-2-hydroxy-4-methylpentanoic acid ("OH-leucine", see 21), and of (S)-2-hydroxy-6-aminohexanoic acid ("OH-lysine", see 22).Some of these products are further converted to CH3- or CF3-substituted γ- and δ- lactones of (R)- or (S)-confuguration (14, 16-19), or to an enantiomerically pure derivative of (R)-1-hydroxy-2-oxocyclopentane-1-carboxylic acid (see 24).Possible uses of these new chiral building blocks for the synthesis of natural products and their CF3 analogues (brefeldin, sulcatol, zearalenone) are discussed.The olfactory properties of (R)- and (S)-δ-caprolactone (18) are compared with those of (R)-6,6,6-trifluoro-δ-caprolactone (19).
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Doi:10.1002/hlca.200590117
(2005)Doi:10.1016/S0040-4039(00)61750-1
(1993)Doi:10.1021/ol0623926
(2006)Doi:10.1080/15533174.2012.753623
(2013)Doi:10.1021/jo015526w
(2001)Doi:10.1055/s-2004-837290
(2005)