Iodine(V) reagents in organic synthesis. Part 1. Synthesis of polycyclic heterocycles via Dess-Martin periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction.
The scope, generality, and mechanism of the Dess-Martin periodinane-mediated cyclization reaction of unsaturated anilides discovered during the total synthesis of the CP-molecules (phomoidrides A and B) are delineated. A plethora of heterocyclic compounds are accessible by employing gamma,delta-unsaturated amides (derived from anilines and carboxylic acids), urethanes, or ureas (derived from isocyanates and allylic alcohols and amines) as substrates. Optimization of the reaction led to room-temperature conditions, while isotope labeling studies allowed a mechanistic rationale for this cascade reaction.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Baran
P S
PS
Zhong
Y-L
YL
Sugita
K
K
D000813:Anilides / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007455:Iodine / Q000737:chemistry*; D010078:Oxazines / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D014508:Urea / Q000737:chemistry; D014520:Urethane / Q000737:chemistry
D000813:Anilides; D006571:Heterocyclic Compounds; D010078:Oxazines; D011083:Polycyclic Compounds; D014520:Urethane; D014508:Urea; D007455:Iodine; C039203:phenoxazine