Asymmetric Organocatalyzed Cascade Reactions─Merging the pseudo-Halogen and Halogen Effect with Dienamine Catalysis

TY - JOUR

T1 - Asymmetric Organocatalyzed Cascade Reactions─Merging the pseudo-Halogen and Halogen Effect with Dienamine Catalysis

AU - Barløse, Casper Larsen

AU - Faghtmann, Jonas

AU - Bitsch, René Slot

AU - Gbubele, Joseph Daniel

AU - Jørgensen, Karl Anker

PY - 2023/2

Y1 - 2023/2

N2 - The combination of asymmetric organocatalysis with the (pseudo)-halogen effect enables the formation of chiral norcarane scaffolds in high yields and selectivities (up to 92% yield, >99% ee, and >95:5 d.r.). This was achieved by reacting (pseudo)-halogenated 3-vinyl chromones with in situ generated chiral dienamines in an inverse electron demand [4 + 2] cycloaddition followed by an intramolecular SN2 reaction. These scaffolds could easily undergo photoinduced rearrangements or lactonization to form intricate chiral ring structures.

AB - The combination of asymmetric organocatalysis with the (pseudo)-halogen effect enables the formation of chiral norcarane scaffolds in high yields and selectivities (up to 92% yield, >99% ee, and >95:5 d.r.). This was achieved by reacting (pseudo)-halogenated 3-vinyl chromones with in situ generated chiral dienamines in an inverse electron demand [4 + 2] cycloaddition followed by an intramolecular SN2 reaction. These scaffolds could easily undergo photoinduced rearrangements or lactonization to form intricate chiral ring structures.

UR - http://www.scopus.com/inward/record.url?scp=85148283046&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c00220

DO - 10.1021/acs.orglett.3c00220

M3 - Letter

C2 - 36787642

SN - 1523-7060

VL - 25

SP - 1209

EP - 1213

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -