2007
DOI: 10.1002/ejoc.200600711
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A New Target for Highly Stereoselective Katsuki–Sharpless Epoxidation – One‐Pot Synthesis of C2‐Symmetric 2,2′‐Bioxiranes

Abstract: The double asymmetric Katsuki-Sharpless epoxidation of a conjugated diallyl alcohol affords excellent enantioselectivity (Ͼ97 % ee), the product being isolated as the stable p-nitrobenzoate 5a or tosylate 5b. The optical purities of the chiral epoxides were determined by HPLC on chiral columns, while the molecular structures of compounds 5a and 7 and the ab-

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Cited by 14 publications
(4 citation statements)
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References 16 publications
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“…Arylmethylidene succinates represent interesting building blocks for the preparation of synthetic targets and natural products. Thus, this class of substances were used as synthons for the preparation of γ‐butyrolactones, 1,4‐diphenylbutadiene derivatives and 2,3‐butandioles . Furthermore, they are excellent precursors of chiral benzyl succinates via asymmetric hydrogenation …”
Section: Introductionmentioning
confidence: 99%
“…Arylmethylidene succinates represent interesting building blocks for the preparation of synthetic targets and natural products. Thus, this class of substances were used as synthons for the preparation of γ‐butyrolactones, 1,4‐diphenylbutadiene derivatives and 2,3‐butandioles . Furthermore, they are excellent precursors of chiral benzyl succinates via asymmetric hydrogenation …”
Section: Introductionmentioning
confidence: 99%
“…COD was distilled and degassed; triethylamine was degassed. (2R,5R)-and (2S,5S)-1-hydroxy-1-oxo-2,5-diphenylphospholane, [37] (2R,5R)-2,5-dimethyl-1-phenylphospholane, [38] [RhA C H T U N G T R E N N U N G (cod) 2 ]BF 4 , [39] [AuClA C H T U N G T R E N N U N G (tht)], [40] [AuC 6 F 5 A C H T U N G T R E N N U N G (tht)], [41] [Au F MesA C H T U N G T R E N N U N G (tht)], [42] MAC, [43] MAA, [44] MAB, [45] and DMPI [46] were prepared according to literature procedures. All other chemicals were used as received from the supplier without further purification.…”
Section: Methodsmentioning
confidence: 99%
“…Therefore, for achieving to better condition conversion of different alcohols into corresponding aldehydes and ketones was performed with different catalyst [1]. In this manner, variety of homogeneous catalysts has been reported for oxidation of alcohol [14][15][16][17][18][19][20]. But the homogeneous catalysts have disadvantages such as di culty in the catalyst recovery and also contamination of the reaction media with metal species.…”
Section: Introductionmentioning
confidence: 99%