J. L. Belletire

Oxidative coupling of carboxylic acid dianions

Abstract The conditions, scope, and stereochemical consequences of a versatile approach to succinic acid derivatives are described.

Free radical cyclizations leading to four-membered rings. I, Beta-lactam production using tributyltin hydride

Abstract Use of HSnBu3 for the reductive cyclization of suitable enamides having a bromide substituent alpha to the carbonyl group affords beta-lactams in good yields.

Direct butyrolactone production using tin hydride

Use of HSnBu3 for the reductive cyclization of suitable alpha-bromo allylic esters affords 2,3-disubstituted butyrolactones.

Oxidative coupling. : II. The total synthesis of enterolactone

Abstract Oxidative coupling of 3-methoxyhydrocinnamic acid dianion with molecular iodine forms the key step in an efficient synthesis of enterolactone.

Oxidative coupling. : III. The duco reaction

Abstract Acylsulfonamide dianions function as efficient synthetic intermediates and are especially suitable for Doubly Unsymmetrical Carbanion Oxidation.

Oxidative Coupling the Toluic Acid Dianion System

Abstract The behavior of all three toluic acid isomers upon treatment with two equivalents of base followed by the addition of iodine-containing reagents is described.

Dianion-Based Methodology for the Preparation of 2,3-Disubstitutrd Butyrolactones

Abstract Unsymmetricai coupling utilizing the reaction of acylsulfonamide dianions with alpha-iodocarboxylate salts followed by a sequence consisting of selective reduction of the carboxylic acid group, hydrolysis of the acylsulfonamide, and spontaneous ring closure affords 2,3-disubstituted butyrolactones.

A Useful Approach to Primary Amines

Abstract Smooth reduction of acylsulfonamides to sulfonamides by borane, when coupled to standard sulfonamide cleavage procedures, provides a general route to primary amines.

A Facile Synthesis of Phenylacetic Acids from Aryl Ketones

Abstract Recently, we sought a generally applicable route to cyclic phenyl-acetic acids of type 1 employing the corresponding readily accessible aryl ketones 2.

A Key Intermediate for the Synthesis of Antitumor Lignan Prototypes

Abstract Procedures are described for the convenient generation of an iodinated carboxylic acid possessing considerable utility as a precursor to several biologically active lignans.