TY - JOUR
T1 - Gold(I)-Catalysed Hydroarylation of 1,3-Disubstituted Allenes with Efficient Axial-to-Point Chirality Transfer
AU - Sutherland, Daniel R.
AU - Kinsman, Luke
AU - Angiolini, Stuart M.
AU - Rosair, Georgina M.
AU - Lee, Ai-Lan
N1 - VIP paper
PY - 2018/5/11
Y1 - 2018/5/11
N2 - 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.
AB - 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.
U2 - 10.1002/chem.201800209
DO - 10.1002/chem.201800209
M3 - Article
C2 - 29542832
SN - 0947-6539
VL - 24
SP - 7002
EP - 7009
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 27
ER -