Journal
TETRAHEDRON LETTERS
Volume 50, Issue 33, Pages 4710-4713Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.06.010
Keywords
Reductive ring opening; Phthalan; DTBB-catalysed lithiation; Chiral sulfinylimines; Organozincates; Diastereoselective addition
Categories
Funding
- Spanish Ministerio de Educacion y Ciencia [CSD2007-00006, CTQ2004-01261]
- University of Alicante
Ask authors/readers for more resources
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 ZnMe2 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 3-substituted tetrahydroisoquinolines 6. (C) 2009 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available