Anti-Markovnikov hydroazidation of unactivated alkenes using ABX–N3 as an initiator has been developed at room temperature,wherein hydrogen azide(HN3)acts as both hydrogen and azidating agent.Notably,the HN3 reagent ...Anti-Markovnikov hydroazidation of unactivated alkenes using ABX–N3 as an initiator has been developed at room temperature,wherein hydrogen azide(HN3)acts as both hydrogen and azidating agent.Notably,the HN3 reagent was generated from azidotrimethylsilane(TMSN3)and acetic acid in situ.The reaction itself displays broad substrate scope,good yields and excellent regioselectivities.展开更多
We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts.A simple chiral primary-tertiary diamine catalyst derived from lphenylala...We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts.A simple chiral primary-tertiary diamine catalyst derived from lphenylalanine was found to readily promote this aza-Michael addition reaction with enamine protonation as the key stereogenic step,thus enabling the effective synthesis of α-chiral β-azido ketones with good yields and moderate enantioselectivities.展开更多
基金supported by the National Basic Research Program of China(973-2015CB856600)the National Natural Science Foundation of China(21532009,21821002,21790330,21761142010)+2 种基金the Science and Technology Commission of Shanghai Municipality(17XD1404500,17QA1405200,17JC1401200)the strategic Priority Research Program(XDB20000000)the Key Research Program of Frontier Science(QYZDJSSW-SLH055)of the Chinese Academy of Sciences
文摘Anti-Markovnikov hydroazidation of unactivated alkenes using ABX–N3 as an initiator has been developed at room temperature,wherein hydrogen azide(HN3)acts as both hydrogen and azidating agent.Notably,the HN3 reagent was generated from azidotrimethylsilane(TMSN3)and acetic acid in situ.The reaction itself displays broad substrate scope,good yields and excellent regioselectivities.
基金National Natural Science Foundation of China(NSFC Nos.21390400,21521002 and 21502198)the Ministry of Science and Technology,Chinese Academy of Sciences(No.QYZDJSSW-SLH023)for generous financial supportsupported by National Program for Support of Top-notch Young Professionals,CAS Youth Innovation Promotion Association and CAS onehundred talented program(D)
文摘We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts.A simple chiral primary-tertiary diamine catalyst derived from lphenylalanine was found to readily promote this aza-Michael addition reaction with enamine protonation as the key stereogenic step,thus enabling the effective synthesis of α-chiral β-azido ketones with good yields and moderate enantioselectivities.
