New and efficient methodology for the synthesis of chiral mono- and ditellurides

An efficient methodology for the synthesis of chiral mono- and ditellurides derived from monoterpenes has been developed. A new approach for the preparation of sodium telluride and sodium ditelluride is proposed. Optically active compounds with p-menthane, carane, and pinane skeletons were obtained by a one-pot synthesis with good yields.

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(1S,1′S)-(+)-Dineomenthyl ditellurideC20H38Te2Ee >99%[α]D25 = +318.9 (c 0.26, CHCl3)Source of chirality: (−)-mentholAbsolute configuration: (1S,1′S)

(1R,1′R)-(−)-Dimenthyl ditellurideC20H38Te2Ee >99%[α]D26 = −260.0 (c 0.51, CHCl3)Source of chirality: (−)-mentholAbsolute configuration: (1R,1′R)

(1R,1′R)-(+)-Bis(4-caranyl) ditellurideC20H34Te2Ee >99%[α]D26 = +214.7 (c 0.34, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1R,1′R)

(1S,1′S)-(−)-Bis(4-isocaranyl) ditellurideC20H34Te2Ee >99%[α]D26 = −153.2 (c 0.29, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1S,1′S)

(1S,1′S)-(−)-Dimyrtanyl ditellurideC20H34Te2Ee >96%[α]D26 = −89.3 (c 0.47, CHCl3)Source of chirality: (−)-β-pineneAbsolute configuration: (1S,1′S)

(1S,1′S)-(+)-Dineomenthyl tellurideC20H38TeEe >99%[α]D20 = +130.3 (c 0.33, CHCl3)Source of chirality: (−)-mentholAbsolute configuration: (1S,1′S)

(1R,1′R)-(+)-Bis(4-caranyl) tellurideC20H34TeEe >99%[α]D24 = +80.4 (c 0.75, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1R,1′R)

(1S,1′S)-(−)-Dimyrtanyl tellurideC20H34TeEe >99%[α]D24 = −68.6 (c 0.70, CHCl3)Source of chirality: (−)-β-pineneAbsolute configuration: (1S,1′S)