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- Title
Copper‐Catalyzed Enantioselective Doyle–Kirmse Reaction of Azide‐Ynamides via α‐Imino Copper Carbenes.
- Authors
Liu, Xin; Liu, Li‐Gao; Chen, Can‐Ming; Li, Xiao; Xu, Zhou; Lu, Xin; Zhou, Bo; Ye, Long‐Wu
- Abstract
[2,3]‐Sigmatropic rearrangement reaction involving sulfonium ylide (Doyle–Kirmse reaction) generated from metal carbenes represents one of the powerful methods for the construction of C(sp3)−S and C−C bonds. Although significant advances have been achieved, the asymmetric versions via the generation of sulfonium ylides from metal carbenes have been rarely reported to date, and they have so far been limited to diazo compounds as metal carbene precursors. Here, we describe a copper‐catalyzed enantioselective Doyle–Kirmse reaction via azide‐ynamide cyclization, leading to the practical and divergent assembly of an array of chiral [1,4]thiazino[3,2‐b]indoles bearing a quaternary carbon stereocenter in generally moderate to excellent yields and excellent enantioselectivities. Importantly, this protocol represents a unique catalytic asymmetric Doyle–Kirmse reaction via a non‐diazo approach and an unprecedented asymmetric [2,3]‐sigmatropic rearrangement via α‐imino metal carbenes.
- Subjects
METAL carbenes; METAL compounds; REARRANGEMENTS (Chemistry); DIAZO compounds; CARBENES; INDOLE compounds; INDOLE derivatives; COPPER
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 10, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202216923