Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes

• An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to α,β-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the β-carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the α-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino−thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to α,β-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

carbonyl-compounds

michael addition

cyclic enones

catalyst

organocatalysis

ether

Publikations- och innehållstyp

ref (ämneskategori)

art (ämneskategori)