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Synthesis of cis-3-hydroxypipecolic acid via SmI2-mediated cyclization of aldehydo β-aminovinyl sulfoxides

✍ Scribed by Hea Seung Chung; Won Kyo Shin; Soo Young Choi; Young Keun Chung; Eun Lee


Book ID
104097201
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
271 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis


Stereoselective synthesis of cis-3-hydroxypipecolic acid was achieved via chirality transfer in the SmI 2mediated cyclization reactions of aldehydo b-aminovinyl sulfoxides.


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The boron trifluoride-etherate mediated cyclization of 2-arylthio-ketones la-h at ambient temperature gave 3-aryl-substituted benzothiophenes 2a-h in excellent yield. None of the rearranged 2-aryl-substituted benzothiophenes were observed.