Luca Parlanti

Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: a short synthesis of (−)-roccellaric acid

Abstract (−)-Roccellaric acid and variously substituted succinates are obtained through direct asymmetric carbolithiation of 2-phenylselenofumarate derivatives, followed by reaction with suitable electrophiles.

Hypervalent iodine chemistry: Novel and direct thiocyanation of alkenes using [bis(acetoxy)iodo]benzene/trimethylsilyl isothiocyanate reagent combination. Synthesis of 1,2-dithiocyanates

Abstract Novel and direct thiocyanation of alkenes using [bis(acetoxy)iodo]benzene/trimethylsilyl isothiocyanate reagent combination has been developed.

Direct amino-phenylselenylation of enoates: An easy route to α-phenylseleno-β-amino esters and β-lactams

Abstract A “one-pot” procedure to obtain α-phenylseleno-β-amino esters from the corresponding enoates is described. The target compounds are useful synthetic tools and direct precursors of new α-phenylseleno-β-lactams, which can be easily transformed into their α-alkylidene analogues. A direct procedure to obtain α-phenylseleno-β-amino esters from the corresponding enoates is described. The target compounds are direct precursors of new α-phenylseleno-β-lactams. Download : Download full-size image

The binary reagent PhSeClZnCl2: a powerful chloro-phenylselenenylating agent of electrophilic olefins

Abstract The binary reagent PhSeClZnCl 2 was found to be powerful for the stereocontrolled conversion of highly electrophilic olefins, such as maleate and fumarate esters, into the corresponding chloro phenylseleno derivatives in very high yields. Other olefins, such as methyl acrylate and methyl vinyl ketone, react virtually instantaneously.

SELENIUM-DIRECTED CONJUGATE ADDITION OF AMINES TO DIMETHYL 2-PHENYLSELENO FUMARATE : REGIO AND DIASTEREOSELECTIVE SYNTHESIS OF 2-PHENYLSELENO-3-AMINO SUCCINATES

Abstract Dimethyl 2-phenylseleno fumarate 1 acts as a strong Michael acceptor of amines, providing the corresponding 2-phenylseleno-3-amino succinates 2a and 2b in very high yields with complete regio- and good diastereoselectivity.

Hypervalent iodine induced nucleophilic additions to alkenes: Synthesis of 1,2-diperchlorates

Abstract a novel iodine (III) reagent has been developed by the BAIB/Mg(ClO 4 ) 2 reagent combination. Reaction of this reagent with alkenes yielded 1,2-diperchlorates.

Reactions of 2,5-dihydro-2,5-dimethoxy-furan with phenylselenenylchloride: Regio- and stereocontrolled generation of highly functionalized C4 building-blocks

Abstract An efficient protocol for stereo- and regiocontrolled synthesis of small polyfunctional molecules is presented. The stereospecific addition of PhSeCl to 2,5-dihydro-2,5-dimethoxy-furan 1 in solvents, such as methylene chloride and methanol, gives cyclic and linear acetals 2 and 3, depending on the solvent used. Emphasis is given to the regiocontrolled hydrolysis of acetal groups for the preparation of stereodefined and highly functionalized C4 synthons, such as 8, 9 and 13.

Tandem Michael-aldol induced ring closure of dimethyl 2-phenylselenofumarate: a diastereoselective entry to novel 4-phenylseleno butano-4-lactone derivatives, versatile precursors of naturally occurring compounds

Tandem Michael-aldol induced ring closure of dimethyl 2-phenylsenofumarate gives, with good yields and diastereoselectivities, highly substituted 4-phenylselenobutano-4-lactones, which can be further transformed into naturally occurring substances.