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Stereoselective synthesis of 3-substituted tetrahydroisoquinolines from phthalan and chiral N-sulfinylimines

✍ Scribed by Daniel García; Benjamín Moreno; Tatiana Soler; Francisco Foubelo; Miguel Yus

Book ID
104096669
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
872 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of the dianionic intermediate [resulting from the reductive opening of phthalan (1) with lithium] with chiral N-tert-butylsulfinyl aldimines 3 in the presence of ZnMe 2 gives, after hydrolysis, N-tert-butylsulfinyl amino alcohols 4 with high diastereoselectivity. Successive treatment of compounds 4 with hydrogen chloride in methanol, thionyl chloride in chloroform and sodium hydroxide yields 3substituted tetrahydroisoquinolines 6.

📜 SIMILAR VOLUMES

Synthesis of substituted tetrahydroisoqu
Synthesis of substituted tetrahydroisoquinolines and benzo[d]azepines from phthalan or isochroman and N-silylaldimines
✍ F. Foubelo; C. Gómez; A. Gutiérrez; M. Yus 📂 Article 📅 2000 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 309 KB

## Abstract The 4,4′‐di‐__tert__‐butylbiphenyl‐catalyzed lithiation of phthalan (**1a**) and isochroman (**1b**) in THF at 0°C affords the corresponding functionalized benzyllithiums **2**, which by reaction with __N__‐silylaldimines yield, after acid‐base work‐up, the expected amino alcohols **3**

ChemInform Abstract: 2-Substituted-1,2,3
ChemInform Abstract: 2-Substituted-1,2,3,4-tetrahydroisoquinolines and Chiral 3-Carboxyl Analogues from N-Benzotriazolylmethyl-N-phenethylamines.
✍ Alan R. Katritzky; Hai-Ying He; Rong Jiang; Qiuhe Long 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v