Organocatalytic Enantioselective Addition of Thiols to Ketimines Derived from Isatins

Organic Letters

Volumn 17, Issue 1, 2015, Pages 106-109

  Nakamura, Shuichi ^a   Takahashi, Shun ^a   Nakane, Daisuke ^a   Masuda, Hideki ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; IMINE; ISATIN; KETIMINE; NITRILE; THIOL DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; CINCHONA ALKALOIDS; IMINES; ISATIN; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 84924339043     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503309s     Document Type: Article

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53. We also examined the reaction using various cinchona alkaloids, such as quinine, quinidine, cinchonine, and cinchonidine; however, the reaction afforded product 4 with lower enantioselectivity than when 3c was used.
54. The reaction using 10 mol % of TMSOH cannot improve the enantioselectivity of the product.
55. The reaction of nonprotected isatin ketimine with 2a using 3c also afforded the product with high enantioselectivity but in low yield (27%, 86% ee).
56. The reaction of 1d with benzenethiol also gave the product, but it was not a stable compound.
57. We also examined the transformation of products such as removal of the Adoc group or the cyclization reaction between ester groups with amides, but these compounds are not so stable.
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