906542-95-8Relevant articles and documents
Gold(I)-Catalysed Hydroarylation of 1,3-Disubstituted Allenes with Efficient Axial-to-Point Chirality Transfer
Sutherland, Daniel R.,Kinsman, Luke,Angiolini, Stuart M.,Rosair, Georgina M.,Lee, Ai-Lan
supporting information, p. 7002 - 7009 (2018/04/30)
Hydroarylation of enantioenriched 1,3-disubstituted allenes has the potential to proceed with axial-to-point chirality transfer to yield enantioenriched allylated (hetero)aryl compounds. However, the gold-catalysed intermolecular reaction was previously reported to occur with no chirality transfer owing to competing allene racemisation. Herein, we describe the development of the first intermolecular hydroarylations of allenes to proceed with efficient chirality transfer and summarise some of the key criteria for achieving high regio- and stereoselectivity.
Chirality Transfer in Gold(I)-Catalysed Hydroalkoxylation of 1,3-Disubstituted Allenes
Webster, Stacey,Sutherland, Daniel R.,Lee, Ai-Lan
, p. 18593 - 18600 (2016/12/16)
Gold(I)-catalysed intermolecular hydroalkoxylation of enantioenriched 1,3-disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemisation. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported here, exploiting conditions that suppress allene racemisation. A full substrate scope study reveals that excellent regio- and stereoselectivities are achieved when a σ-withdrawing substituent is present.
Regio- And stereoselective synthesis of alkyl allylic ethers via gold(l)-catalyzed intermodular hydroalkoxylation of allenes with alcohols
Zhang, Zhibin,Widenhoefer, Ross A.
supporting information; experimental part, p. 2079 - 2081 (2009/04/10)
Reaction of 1-phenyl-1,2-butadiene with 2-phenyl-1-ethanol catalyzed by a 1:1 mixture of a gold(l) W-heterocyclic carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio-
