TY - JOUR
T1 - Catalytic Asymmetric Vinylogous Prins Cyclization
T2 - A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans
AU - Xie, Youwei
AU - Cheng, Gui Juan
AU - Lee, Sunggi
AU - Kaib, Philip S.J.
AU - Thiel, Walter
AU - List, Benjamin
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/11/9
Y1 - 2016/11/9
N2 - We describe the design and development of the first catalytic asymmetric vinylogous Prins cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphorimidate (IDPi) catalyst is used. With a racemic dienyl alcohol, the reaction proceeds via a kinetic resolution. DFT calculations suggest an explanation for unusually high stereoselectivity.
AB - We describe the design and development of the first catalytic asymmetric vinylogous Prins cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphorimidate (IDPi) catalyst is used. With a racemic dienyl alcohol, the reaction proceeds via a kinetic resolution. DFT calculations suggest an explanation for unusually high stereoselectivity.
UR - http://www.scopus.com/inward/record.url?scp=84994527376&partnerID=8YFLogxK
U2 - 10.1021/jacs.6b09129
DO - 10.1021/jacs.6b09129
M3 - Article
AN - SCOPUS:84994527376
SN - 0002-7863
VL - 138
SP - 14538
EP - 14541
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 44
ER -