Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives

TY - JOUR

T1 - Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives

AU - Poulsen, Pernille H.

AU - Li, Yang

AU - Lauridsen, Vibeke H.

AU - Jørgensen, Danny K.B.

AU - Palazzo, Teresa A.

AU - Meazza, Marta

AU - Jørgensen, Karl Anker

PY - 2018/8/13

Y1 - 2018/8/13

N2 - A novel reaction that provides chiral allenes by amino catalytic activation of either aldehydes or α,β-unsaturated aldehydes for reaction with alkynyl-substituted enones is presented. The reaction forms a variety of trisubstituted allenes in high yields and with excellent stereoselectivities. The utility of the reaction concept is demonstrated by the synthesis of chiral furan derivatives in high yields and stereoselectivities.

AB - A novel reaction that provides chiral allenes by amino catalytic activation of either aldehydes or α,β-unsaturated aldehydes for reaction with alkynyl-substituted enones is presented. The reaction forms a variety of trisubstituted allenes in high yields and with excellent stereoselectivities. The utility of the reaction concept is demonstrated by the synthesis of chiral furan derivatives in high yields and stereoselectivities.

KW - allenes

KW - asymmetric catalysis

KW - chirality

KW - furans

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/85050338810

U2 - 10.1002/anie.201806238

DO - 10.1002/anie.201806238

M3 - Journal article

C2 - 29917329

AN - SCOPUS:85050338810

SN - 1433-7851

VL - 57

SP - 10661

EP - 10665

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -