Practical and robust method for the preparation of Seebach and Fráter's chiral template, cis-2-substituted 5-methyl(or phenyl)-1,3-dioxolan-4-ones

Synthesis

Volumn , Issue 22, 2006, Pages 3915-3917

  Nagase, Ryohei ^a   Oguni, Yumiko ^a   Misaki, Tomonori ^a   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

(S) lactic acid; (S) mandelic acid; 2,5 disubstituted 1,3 dioxolan 4 ones; Acid catalyst; Cyclocondensation

Indexed keywords

COLUMN CHROMATOGRAPHY; DISTILLATION; NITROGEN COMPOUNDS; REACTION KINETICS; ROBUSTNESS (CONTROL SYSTEMS); SUBSTITUTION REACTIONS;

(S)-LACTIC ACID; (S)-MANDELIC ACID; ACID CATALYST; CYCLOCONDENSATION;

STEREOCHEMISTRY;

2 (4 CHLOROPHENYL) 5 METHYL 1,3 DIOXOLAN 4 ONE; 2 (TERT BUTYL) 5 METHYL 1,3 DIOXOLAN 4 ONE; 2 (TERT BUTYL) 5 PHENYL 1,3 DIOXOLAN 4 ONE; KETONE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; DISTILLATION; PURIFICATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 33845303114     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950295     Document Type: Article

References (19)

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17. In our hands, comparable experiments using pentane and heptane (bp 98°C) as solvents revealed that they have a significant effect on the stereoselectivity; cis/trans = 97:3 (pentane) and 54:46 (heptane). The direct method largely depends on the reaction temperature of azeotropic boiling points.
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