Stereospecific desulfinylation of .ALPHA.,.BETA.-epoxy sulfoxides with butyllithium. A new synthesis of epoxides and allylic alcohols from carbonyl compounds.
スポンサーリンク
概要
- 論文の詳細を見る
Desulfinylation of α,β-epoxy sulfoxides, easily prepared from carbonyl compounds and 1-chloroalkyl phenyl sulfoxide, with 1 equivalent of butyllithium at low temperature gave epoxides in good yields. The similar α,β-epoxy sulfoxides having an arylmethyl group at the α-position gave 3-aryl-allylic alcohols upon treatment with excess butyllithium at −70 °C. These reactions offer a simple and useful approach to the synthesis of epoxides and 3-aryl-allylic alcohols from a carbonyl compound.
- 公益社団法人 日本化学会の論文
著者
-
Satoh Tsuyoshi
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
-
Yamakawa Koji
Faculty Of Pharmaceutical Science Science University Of Tokyo
-
Kaneko Youhei
Faculty of Pharmaceutical Sciences, Science University of Tokyo
関連論文
- Ligand Exchange Reaction of Sulfoxides in Organic Synthesis. A Novel Method for Synthesizing Acetylenes from Carbonyl Compounds through β-Trifluoromethanesulfonyloxy Vinyl Sulfoxides
- Lethium-Chlorine Exchange Reaction of α-Chloro α-Sulfonyl Ketones
- PB146 A NOVEL APPROACH TO THE SYNTHESIS OF CHIRAL EPOXIDES : VERY SHORT SYNTHESIS OF (+)-DISPARLURE, THE SEX ATTRACTANT OF FEMALE GYPSY MOTH
- Synthesis and Some Spectroscopic Properties of Porphyrin Derivatives Connected with Nucleobases (Adenine, Thymine, Guanine and Cytosine)by Alkanamide Chains
- Porphyrins Coupled with Nucleoside Bases. Synthesis and Characterization of Ether-Linked Adenine-Thymine and Guanine-Cytosine Derivatives
- Synthesis and Molecular Structure of [4][3_4](1,2,3,4,5)Ferrocenophane
- Microbial Formation of Lumisantonin from (-)-α-Santonin : Studies on Microbial Transformations (XX)
- Microbial Hydroxylation of 11,13-Dehydrosantonin by Aspergillus niger : Studies on Microbiological Transformation (XXVIII).
- Microbial Hydroxylation of (-)-α-Santonin by Aspergillus niger : Studies on Microbial Transformations(XXIV)
- X-ray crystal structure of 7,16,24,33-tetrathia[3]paracyclo[3](1,3)-ferroceno[3]paracyclo[3](1,3)ferrocenophane.
- Synthesis of Antiprismatic (5.5)Ferrocenophane ((5)(1,1')(5)(3,4')Ferrocenophane).
- Nucleophilic Ring-Opening of Chlorooxiranes: A New Synthesis of .ALPHA.-Hydroxy .ALPHA.'-Substituted Ketones from Carbonyl Compounds and 1-Chloroalkyl p-Tolyl Sulfoxides.
- Stereospecific desulfinylation of .ALPHA.,.BETA.-epoxy sulfoxides with butyllithium. A new synthesis of epoxides and allylic alcohols from carbonyl compounds.
- .ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in organic synthesis. X. An improved synthesis of .ALPHA.-.BETA.-unsaturated carbonyl compounds from carbonyl compounds with carbon homologation through .ALPHA.,.BETA.-epoxy sulfoxides.
- .ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in organic synthesis. II. A novel synthesis of .ALPHA.-sulfenylated ketones and .ALPHA.-sulfenylated aldehydes from .ALPHA.,.BETA.-epoxy sulfoxides.
- .ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in organic synthesis. IV. A novel synthesis of .ALPHA.-acetoxy ketones from .ALPHA.,.BETA.-epoxy sulfoxides.
- Synthesis and X-ray crystal structure of [54](1,2,3,4)ferrocenophane.
- Synthesis of [52](1,2)ferrocenophane.
- .ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in organic synthesis. I. A novel synthesis of dialkyl ketones and a synthesis of aldehydes from ketones by one carbon elongation.
- .ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in organic synthesis. XVI. A novel synthesis of 2-acyl cyclic ethers and 3-keto cyclic ethers including spiro cyclic ethers via intramolecular ring-opening of .ALPHA.,.BETA.-epoxy sulfoxides with hyd
- .ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in Organic synthesis. IX A novel synthesis of alkyl vinyl ketones and divinyl ketones from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide as a three-carbon homologating agent.