Open AccessOrthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
Author(s) -
Andrea Serafino,
Davide Balestri,
Luciano Marchiò,
Max Malacrìa,
Étienne Derat,
Giovanni Maestri
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02193
Subject(s) - chemistry , allene , sulfonyl , product (mathematics) , visible spectrum , combinatorial chemistry , carbon fibers , carbon chain , stereochemistry , photochemistry , organic chemistry , catalysis , optoelectronics , algorithm , computer science , alkyl , geometry , mathematics , physics , composite number
Enallenes can be readily converted into two families of 3.2.0 (hetero)bicycles with high diastereoselectivities through the combination of visible light with a suitable Ir(III) complex (1 mol %). Two complementary pathways, namely, a photocycloaddition versus a radical chain, can then take place. Both manifolds grant complete regiocontrol of the allene difunctionalization. This is accompanied by an original 1,3-group shift using sulfonyl allenamides that deliver a congested tetrasubstituted headbridging carbon in the corresponding product.