Enantiocontrol in tandem allylic sulfonium ylide generation and [2,3] sigmatropic rearrangement catalyzed by chiral dirhodium(II) complexes

Authors
Kitagaki, S Yanamoto, Y Okubo, H Nakajima, M Hashimoto, S
Citation
S. Kitagaki et al., Enantiocontrol in tandem allylic sulfonium ylide generation and [2,3] sigmatropic rearrangement catalyzed by chiral dirhodium(II) complexes, HETEROCYCLE, 54(2), 2001, pp. 623
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
54
Issue
2
Year of publication
2001
Database
ISI
SICI code
0385-5414(20010201)54:2<623:EITASY>2.0.ZU;2-X
Abstract
Tandem sulfonium ylide formation and [2,3] sigmatropic rearrangement sequen ce from allylic sulfides and diazoacetates has been effected by using dirho dium(II) tetrakis [3(S)-phthalimido-2-piperidinonate], Rh-2(S-PTPI)(4), as a chiral catalyst, displaying enantioselectivities of up to 58%. It has bee n demonstrated that the [2,3] sigmatropic rearrangement proceeds through ch iral, nonracemic free sulfonium ylides dissociated from the dirhodium(II) c omplex.