Journal
ORGANIC LETTERS
Volume 25, Issue 28, Pages 5248-5252Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01723
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Enantioconvergent iso-Pictet-Spengler reactions of chiral racemic ss-formyl esters and a ss-keto ester are reported, leading to the formation of complex tetrahydro-& gamma;-carbolines bearing two contiguous stereocenters. These reactions are catalyzed by a chiral thiourea and benzoic acid cocatalytic system, representing unusual nonhydrogenative stereoconvergent additions to racemic & alpha;-stereogenic-ss-dicarbonyls. The transformation of the products to chiral aminoalcohols and carbamates is also demonstrated.
Enantioconvergent iso-Pictet-Spenglerreactionsof chiral racemic ss-formyl esters and a ss-keto ester arereported, providing complex tetrahydro-& gamma;-carbolines containingtwo contiguous stereocenters. The reactions are catalyzed by a chiralthiourea and benzoic acid cocatalytic system and constitute rare casesof nonhydrogenative stereoconvergent additions to racemic & alpha;-stereogenic-ss-dicarbonyls.Elaboration of the products to chiral aminoalcohols and carbamatesis demonstrated.
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