55164-54-0Relevant articles and documents
Rhodium catalyzed C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates and analogs
Yang, Xuan,Kong, Wei-Yu,Gao, Jia-Ni,Cheng, Li,Li, Nan-Nan,Li, Meng,Li, Hui-Ting,Fan, Jun,Gao, Jin-Ming,Ouyang, Qin,Xie, Jian-Bo
, p. 12707 - 12710 (2019/10/28)
The C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates with aryl boronic acids catalyzed by a rhodium complex was studied with a "conjugate addition/β-C cleavage/protonation" strategy.
α-(N-carbamoyl)alkylcuprate chemistry in the synthesis of nitrogen heterocycles
Dieter, R. Karl,Lu, Kai
, p. 847 - 855 (2007/10/03)
The conjugate adducts obtained via coupling of α-(N-carbamoyl)alkylcuprates with α,β-ynoates, α-allenyl esters, or α,β-enoates or enimides undergo N-Boc deprotection and cyclization onto the ester functionality upon treatment with PhOH/TMSCl, catecholboron bromide, or trimethylsilyl triflate. This two-pot sequence provides synthetic routes to 4-alkylidinepyrrolidine-2-ones, 4-alkylidinepyrrolizidin-2-ones, and 4-alkylidineindolizidin-2-ones via allenyl esters; pyrrolin-2-ones, tetrahydropyrrolizin-2-ones, and tetrahydroindolizin-2-ones via α,β-ynoates; pyrrolidin-2-ones, pyrrolizidin-2-ones, and indolizidin-2-ones via α,β-enoates or α,β-enimides. The reluctance of γ-carbamoyl-α,β-enoates to undergo E/Z isomerization requires the use of (Z)-β-iodo-α,β-enoates readily prepared by the addition of HI to the alkynyl esters for the efficient preparation of pyrrolinones, tetrahydropyrrolizinones, and tetrahydroindolizinones. Utilization of ω-functionalized α,β-ynoates or β-iodo-α,β-enoates allows for cyclization onto the ω-functionality providing for a synthetic route to quinolizidines.
