Gold(I)-Catalyzed Asymmetric Induction of Planar Chirality by Intramolecular Nucleophilic Addition to Chromium-Complexed Alkynylarenes: Asymmetric Synthesis of Planar Chiral (1H-Isochromene and

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• 作者：Masato Murai ; Yumi Sota ; Yu虆ki Onohara ; Jun鈥檌chi Uenishi ; Motokazu Uemura
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：November 1, 2013
• 年：2013
• 卷：78
• 期：21
• 页码：10986-10995
• 全文大小：389K
• 年卷期：v.78,no.21(November 1, 2013)
• ISSN：1520-6904

文摘

Gold(I)-catalyzed asymmetric intramolecular cyclization of prochiral 1,3-dihydroxymethyl-2-alkynylbenzene or 1,3-bis(carbamate)-2-alkynylbenzene tricarbonylchromium complexes with axially chiral diphosphine ligand gave planar chiral tricarbonylchromium complexes of 1H-isochromene or 1,2-dihydroisoquinoline with high enantioselectivity. An enantiomeric excess of the planar chiral arene chromium complexes was largely affected by a combination of axially chiral diphosphine(AuCl)₂ precatalysts and silver salts. In the case of 1,3-dihydroxymethyl-2-alkynylbenzene chromium complexes, a system of segphos(AuCl)₂ with AgBF₄ resulted in the formation of the corresponding antipode.