Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

• Svetlana V. Amosova,
• Andrey A. Filippov,
• Nataliya A. Makhaeva,
• Alexander I. Albanov and
• Vladimir A. Potapov

Beilstein J. Org. Chem. 2020, 16, 515–523, doi:10.3762/bjoc.16.47

• rearrangements occurred by a nucleophilic attack of the selenocyanate anion at two different carbon atoms of the seleniranium intermediate. The efficient regioselective synthesis of alkyl, allyl, 2-propynyl, benzyl, 4-fluorobenzyl, and 2-pyridinylmethyl 1,3-thiaselenol-2-ylmethyl selenides was developed based on

• -thiaselenole; nucleophilic addition; nucleophilic substitution; rearrangement; seleniranium intermediate; Introduction The regio- and stereoselective synthesis of organoselenium compounds based on selenium-centered electrophilic reagents has been one of the most important and effective directions in

• did not occur (Scheme 2). The high anchimeric assistance effect of the selenium atom in thiaselenole 1 is the driving force for the generation of the seleniranium intermediate 2. A fundamental approach to the regio- and stereoselective synthesis of unsaturated functionalized organoselenium compounds

Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation

• Vadim A. Soloshonok and
• Donna J. Nelson

Beilstein J. Org. Chem. 2011, 7, 744–758, doi:10.3762/bjoc.7.85

• in the additions of 2 could not be fully explained by its C2-symmetric structure or by increased seleniranium intermediate stability via coordination to two oxygens in 2 [33]. Thus, compound 3, also with a C2-symmetric structure, provides for even higher stereochemical outcome in the corresponding