In:
Angewandte Chemie, Wiley, Vol. 133, No. 39 ( 2021-09-20), p. 21359-21364
Abstract:
Enantioenriched spiro‐oxiranes bearing three contiguous stereocenters were synthesized using a rhodium‐catalyzed asymmetric addition/aldol/spirocyclization sequence. Starting from a linear substrate, the cascade enabled the formation of a spirocyclic framework in a single step. sp 2 ‐ and sp‐hybridized carbon nucleophiles were found to be competent initiators for this cascade, giving arylated or alkynylated products, respectively. Derivatization studies demonstrated the synthetic versatility of both the epoxide and the alkyne moieties of the products. DFT calculations were used to reconcile spectroscopic discrepancies observed between the solution‐ and solid‐state structures of the products.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v133.39
DOI:
10.1002/ange.202105562
Language:
English
Publisher:
Wiley
Publication Date:
2021
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