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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 33, Number 4
JKCSEZ 33(4)
August 20, 1989

Title	Highly Diastereoselective Aldol-Type Reaction Using 3-Acetylthiazolidine-2-thione 3-아세틸티아졸리딘-2-티온을 이용한 입체선택적인 알돌-축합반응
Author	Tae Myeong Jeong, Ki Hun Park 정태명, 박기훈
Keywords
Abstract	아미노 알콜에서 합성한 티아졸리딘치온 [4-(S)-IPTT, 4(S)-ETT]은 주석을 매개체로한 알돌 축합반응의 키랄 보조제로 이용되었다. Stannous triflate와 3-아세틸티아졸리딘-2-티온을 반응시켜 얻은 2가주석 엔올레이트를 어키랄 알데히드와 반응시켜 β-하이드록시 카르보닐 화합물을 입체선택적으로 얻었다. 이러한 키랄 보조제는 가메탄올 분해반응으로 쉽게 에스터화 되기 때문에 절대구조 동정을 용이하게 하는 장점도 있었다. Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.
Page	426 - 430
Full Text	PDF

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