Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization.
We have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of alpha-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf)(3)) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure.
Yu
Jin-Di
JD
Department of Chemistry, Fudan University, Shanghai 200433, China.
Ding
Wei
W
Lian
Gao-Yan
GY
Song
Ke-Sheng
KS
Zhang
Dan-Wei
DW
Gao
Xiang
X
Yang
Dan
D
D003500:Cyclization; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014466:Ultraviolet Rays
D005609:Free Radicals; D007769:Lactams; D008698:Mesylates; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; C518808:ytterbium(III) triflate