Construct indeno[1,2-b]oxepine or cis-cyclopropylacrylate by sulfur ylides
نویسندگان
چکیده
منابع مشابه
Novel Asymmetrical Dianionic Polyimido-Sulfur(IV)-Ylides
Sulfurdiimides RN=S=NR react in donating solvents with two equivalents of lithiumalkyls to give the dimeric C,N-dilithium-methylenediimidosulfite solvent adducts [(Et2O)Li2{H2CS(NSiMe3)(NBu)}]2 (1) and [(thf)Li2{H8C4S(NBu)2}]2 (2). Firstly, addition of a lithiumalkyl to sulfurdiimide gives the diimidosulfinates [RS(NR )2] (1: R = Me, R = tBu, SiMe3; 2: R = nBu; R = tBu) while in a second step t...
متن کاملReagent controlled addition of chiral sulfur ylides to chiral aldehydes
The degree of reagent and substrate control in the reaction of chiral sulfur ylides with chiral aldehydes has been investigated. Specifically, the reactions of the two enantiomers of the chiral benzyl sulfonium salt 1 with glyceraldehyde acetonide were studied in detail. Of the two new stereogenic centers created, it was found that the C1 stereochemistry was largely controlled by the reagent, w...
متن کاملEnantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
A convergent, nine-step (LLS), enantioselective synthesis of α-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O c...
متن کاملHemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines.
Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.
متن کاملA catalytic cycle for the asymmetric synthesis of epoxides using sulfur ylides.
Since the pioneering work1 of Furukawa in the late 1980s, some examples2 of nonracemic epoxidation have been reported using aromatic aldehydes and chiral sulfur ylides. Enantiopure oxiranes are versatile compounds for organic synthesis. They can be transformed3 into 1,2difunctionalized derivatives by nucleophilic ring opening reactions. Our group has recently developed4 an efficient asymmetric ...
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ژورنال
عنوان ژورنال: RSC Advances
سال: 2020
ISSN: 2046-2069
DOI: 10.1039/d0ra03919e