Convenient access to two enantiomeric oxirane synthons bearing a quaternary gem-dimethyl carbon center: Synthesis of 3S-(+) and 3R-(−)-2,2-dimethyl-3,4-oxo-1-butanol from R-(−)-pantolactone

Lavallée, Pierre; Ruel, Réjean; Grenier, Louis; Bissonnette, Martine

doi:10.1016/s0040-4039(00)84071-x

Cited by 49 publications

(14 citation statements)

References 19 publications

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“…Evaporation of the solvent yielded 90% of 7. mixture refluxed overnight. 15 After cooling, four drops of Et 3 N were added and the solution was dried over Na 2 SO 4 . The solvent was evaporated and the acetonide 6 was obtained in 90% yield.…”

Section: -Cyclohexen-1-ol Acetate (7)mentioning

confidence: 99%

Role of hydrogen migration in the mechanism of acetic acid elimination from MH+ ions of acetates on chemical ionization and collision-induced dissociation

1999

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The elimination of acetic acid from the MH+ ions of acetates of stereoisomeric 2‐methyl‐1‐cyclohexanols and 1‐hydroxy‐trans‐decalins exhibits a significant degree of stereospecificity under isobutane chemical ionization and collision‐induced dissociation (CID) conditions, resulting in more abundant [MH − AcOH]+ ions in the cis‐isomers 4c and 5tc than in their trans‐counterparts 4t and 5tt. These findings suggest the involvement of a 1,2‐hydride shift from the β‐ to the α‐position in the course of the acetic acid elimination from the MH+ ions of the above cis‐acetates, resulting in tertiary carbocation structures. The proposed mechanism of the elimination is supported by a considerable deuterium isotope effect detected in β‐deuterium‐labeled cis‐2‐methyl‐1‐acetoxycyclohexane and by a CID study of the structures of the [MH − AcOH]+ ions obtained from cis‐ and trans‐1,2‐diacetoxycyclohexanes. Copyright © 1999 John Wiley & Sons, Ltd.

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Section: -Cyclohexen-1-ol Acetate (7)mentioning

confidence: 99%

Role of hydrogen migration in the mechanism of acetic acid elimination from MH+ ions of acetates on chemical ionization and collision-induced dissociation

1999

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“…Thus, pantolactone was reduced with LiAlH 4 to triol 11 according to literature procedures. [25] However, it was found that this approach gave poor yields and very problematic purification; therefore, the strategy was modified to first include the protection of 10 as an allyl ether. Using one equivalent of KOtBu, allyl ether 13 was prepared in good yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of an Acyclic C1–C11 Fragment of Peloruside B

et al. 2011

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“…95, No. 234 Thus, reduction of 640 followed by acetalization provided exclusively the CC,CT-pentylidene acetal 641; protection of the Cg hydroxyl, acetal hydrolysis, and subsequent tosylimidazole-mediated epoxide formation then supplied 638. After dithiane cleavage, the stereogenic center at C5 was to be installed by a 1,3-anti selective reduction of a ,&hydroxy ketone.…”

Section: Vandewalle Segment Synthe~es2~~mentioning

confidence: 99%