2.5 anti-1,3-Diols and Polyols via SAMP/RAMP Hydrazones

Propella ether (11-oxatricyclo[,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydroxyethyl)spiro[4.5]decan-6-ol) in 97% yield via carbon skeleton rearrangement.

Armen Zakarian, Huw M. L. Davies et al., J. Am. Chem. Soc. 2014, 136, 17738 [] [] [] []

23. Direct access to heterocyclic scaffolds by new multicomponent Ugi-Smiles couplings. El Kaim, L.; Gizolme, M.; Grimaud, L.; Oble, J. Org. Lett. 2006, 8, 4019-4021.

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14, 1973.oral-rat LD50 2000 mg/kgJournal of Agricultural and Food Chemistry.

70. Ugi-Smiles couplings of 4-substituted pyridine derivatives: a fast access to chloroquine analogues. El Kaim, L.; Grimaud, L.; Pravin, P. Org. Lett. 2012, 14, 476-478.

1,3-propanediol, or a derivative thereof, is used

73. Four-component synthesis of indazole through Ugi-azide coupling. El Kaim, L.; Grimaud, L.; Purumandla, S. R. Synlett 2012, 295-297.

9.2 1,3-Diols via 1-Oxa-2-silacyclopentanes

The high diastereo- and enantioselectivity in the formation of the (R,R) isomer is accounted for by an anti s′E transition state 18.AB - (2R,3S)-3-Allyloxy-3,4,5,6-tetrahydro-2H-pyran-2-methanol was prepared in high yield from tri-O-acetyl-d-glucal, an easily available and cheap chiral source.

Regan J. Thompson et al., J. Am. Chem. Soc. 2014, 136, 17750 [] [] []

74. Palladium catalyzed ring-opening of aminocyclopropyl Ugi adducts. Dos Santos, A.; El Kaim, L.; Grimaud, L.; Ramozzi, R. Synlett 2012, 438-442.

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66. Evidences for the Key-Role of Hydrogen Bonds in SNAr. N. Chéron, L. El Kaïm, L. Grimaud, P. Fleurat-Lessard, Chem. Eur. J. 2011, 17, 14929–14934.

Removal of the protecting group of 2 gave the (R,R) diols 3.

64. Phosphite mediated synthesis of benzimidazoles: a one-pot four-component approach from nitrophenols. El Kaim, L.; Grimaud, L. ; Purumandla, S. P. Eur. J. Org. Chem. 2011, 31, 6177–6180.

S. Breitler and E. M. Carreira*, , 2013, 52, 11168; [][][]

76. Metal-frEe aerobic oxidation of benzazole derivatives. Dos Santos, A.; El Kaim, L. ; Grimaud, L. Org. Biomol. Chem. 2013, 11, 3282-3287.