Preparation of Cyclobutyl Group Carrying Cyclobutanones and Related Synthetic Building Blocks

Dehmlow, Eckehard V.; Kinnius, Joerg; Buchholz, Monika; Hannemann, Dirk

doi:10.1002/(sici)1521-3897(200004)342:4<409::aid-prac409>3.0.co;2-e

Cited by 6 publications

(1 citation statement)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We performed a [2 + 2] cycloaddition using dichloroketone, generated in situ from trichloroacetyl chloride in the presence of activated zinc [46]. Subsequent reduction of the dichloroketone led to 3-Vinylcyclobutanone 11a in 44% over two steps.…”

Section: Resultsmentioning

confidence: 99%

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

Rudroff¹,

Fink

Pydi³

et al. 2016

Monatsh Chem

View full text Add to dashboard Cite

This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer–Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(−)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine.Graphical abstract

show abstract

Section: Resultsmentioning

confidence: 99%

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

Rudroff¹,

Fink

Pydi³

et al. 2016

Monatsh Chem

View full text Add to dashboard Cite

show abstract

Reduction of 3-Substituted 1-Arylcyclobutanols

Kinnius

Dehmlow²

2000

J. prakt. Chem.

Self Cite

View full text Add to dashboard Cite

421In the context of our work on novel model compounds for liquid crystals which contain cyclobutyl groups, [1 -4] we were interested in an effective benzylic alcohol →hydrocar-bon conversion of 1-arylcyclobutanols 1 to give compounds 2. Ideally this should be a one-pot process.Hydrogenolysis as well as elimination/catalytic hydrogenation led to unpleasant product mixtures frequently. Likewise, Olah's method (Pd/cyclohexene/AlCl 3 ) [4] or our own previous procedure (Me 2 NBH 2 /TiCl 4 ) [5] gave unsatisfactory yields oftentimes. When, however, compound 1a was treated with lithium aluminumhydride/aluminum trichloride in tert-butyl methyl ether according to Brewster et al. [6], 2a was obtained in 51% as a 58:42 mixture of trans and cis isomers. Both chemical yield (93%) and stereoselectivity (7:3) where improved when applying a modification of the method of Gribble et al. (NaBH 4 in CF 3 COOH) [7,8].Consequently, this last mentioned procedure was applied to an entire series of 3-substituted 1-arylcyclobutanols 1a -1o. A preponderance of the desired trans isomers (52 -76%) was observed in all cases, and most chemical yields were satisfactory (Table 1) Abstract. A useful and specific method for the the title reaction (1 → 2) involves treatment with NaBH 4 in CF 3 COOH whereas other procedures from the literature yield hard-toseparate mixtures.

show abstract

ChemInform Abstract: Preparation of Cyclobutyl Group Carrying Cyclobutanones and Related Synthetic Building Blocks.

et al. 2000

View full text Add to dashboard Cite

Preparation of Cyclobutyl Group Carrying Cyclobutanones and Related Synthetic Building Blocks.-Unsymmetrically substituted cyclobutyl-cyclobutanes are prepared via vinylcyclobutanes. Two methods are applied. The first method starts with (V) and involves Grignard addition, protection of the hydroxy group, cycloaddition of dichloroketene (II) followed by a reducing step to give a mixture of diastereomers (VII). A second Grignard reaction can introduce a further aryl residue. The second sequence ((XI)→(XV)) involves two methylene Wittig reactions and a dichloroketene cycloaddition. The starting compound (V) is obtained by cycloaddition of dichloroketene (II) to diene (I) after reduction of monoadduct (III). Bisadduct (IV) is new to the literature.

show abstract

Preparation of Cyclobutyl Group Carrying Cyclobutanones and Related Synthetic Building Blocks

Cited by 6 publications

References 12 publications

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

Reduction of 3-Substituted 1-Arylcyclobutanols

ChemInform Abstract: Preparation of Cyclobutyl Group Carrying Cyclobutanones and Related Synthetic Building Blocks.

Contact Info

Product

Resources

About