Chiral Sulfinyl Group Research Articles

Asymmetric Synthesis of Biologically Active Compounds Bearing a Chiral Sulfinyl Group

Abstract The asymmetric synthesis of (R C,SS) and (S C,R S), important intermediates in the synthesis of optically pure Sparsomycin analogs, is discussed. The enantioselective synthesis of both isomers, R and S, of Oxisuran and three of their bioisosters is also described. In both strategies o.p. methanesulfinate esters of DAG were used as starting material.

The Lewis Acid-catalyzed Intramolecular Asymmetric Hetero Diels-Alder Reaction of Chiral a'-Sulfinyl-a,b-unsaturated Ketone. A Chiral Diene Bearing an Optically Active Sulfinylmethyl Group

This paper presents an asymmetric Diels-Alder reaction with a diene bearing a chiral sulfinyl group. The Lewis acid-catalyzed intramolecular asymmetric hetero Diels-Alder reaction of a chiral α'-sulfinyl-α,β-unsaturated ketone derived from 3-methylcitronellal produced optically active 4a,5,6,7,8,8a-hexahydro-1H-2-benzopyran derivatives. On the basis of the stereochemical results obtained, a plausible mechanism for the asymmetric induction is presented

Intramolecular Lewis acid-catalyzed asymmetric hetero-Diels-Alder reactions with dienes bearing chiral sulfinyl groups

A chiral α-sulfinyl α,β-unsaturated ketone served as a chiral diene in intramolecular Lewis acid-catalyzed asymmetric cycloaddition reactions, giving hetero-Diels-Alder reaction products along in some cases with ene reaction products in high optical yields. The reaction pathways for Diels-Alder or ene reactions were readily controlled depending on the Lewis acids used.

A new approach to the asymmetric cyclopropanation via a chiral sulfinyl group

High stereoselectivity and high yield are observed in the Michael addition of dimethyl sulfoxonium methylide to an optically pure methyl α-(p-tolylsulfinyl) acrylate. A novel route to the asymmetric synthesis of electrophilic cyclopropanes.

ChemInform Abstract: Stereochemistry of Asymmetric 1,2‐Rearrangements of Chiral Sulfenylcyclopropanes into Cyclobutane Derivatives. A Novel Entry to Chiral Cyclobutane Systems Using Chiral Sulfinyl Groups.

AbstractReduction of the optically active sulfoxide (I) to give the sulfide (II) with high optical purity is achieved via the hydroxy‐protected derivatives (III).

Stereochemistry of Asymmetric 1,2-Rearrangements of Chiral Sulfenylcyclopropanes into Cyclobutane Derivatives. A Novel Entry to Chiral Cyclobutane Systems Using Chiral Sulfinyl Groups

Abstract Stereochemistry of 1,2-rearrangements in optically active 1-(1-hydroxyalkyl)-1-sulfenylcyclopropane derivatives was determined. Both of the enantiomers underwent smoothly a 1,2-rearrangement of carbon-carbon bonds in cyclopropanes via the mesylates with complete stereospecificity to provide chiral cyclobutane derivatives with high enantiomeric excess.

ChemInform Abstract: Homochiral Fluoroorganic Compounds. Part 10. A New Protocol for the Synthesis of Variously Functionalized α‐Fluoroketones and α‐Fluoroalcohols.

AbstractRemoval of the chiral sulfinyl group of (I) leads to the title ketones (II).

Asymmetric induction by sulfinyl chirality. A total synthesis of (+)-talaromycin A and (−)-talaromycin B

A total synthesis of (+)-talaromycin A and (−)-talaromycin B was accomplished by means of successive asymmetric induction of all chiral centers using a chiral sulfinyl group.