title: Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles.
abstract: The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position.
authors.affiliation: Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. edward.anderson@chem.ox.ac.uk.
authors.forename: V
authors.initials: V
authors.lastname: Chintalapudi
authors.affiliation: Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. edward.anderson@chem.ox.ac.uk.
authors.forename: E A
authors.initials: EA
authors.lastname: Galvin
authors.affiliation: Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. edward.anderson@chem.ox.ac.uk.
authors.forename: R L
authors.initials: RL
authors.lastname: Greenaway
authors.affiliation: Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. edward.anderson@chem.ox.ac.uk.
authors.forename: E A
authors.initials: EA
authors.lastname: Anderson