Construction of CS Bonds with a Quaternary Stereocenter through a Formal Michael Reaction: Asymmetric Synthesis of Tertiary Thiols†
Claudio Palomo Prof. Dr.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorMikel Oiarbide Prof. Dr.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorFlavia Dias
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorRosa López Dr.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorAnthony Linden Dr.
Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland
crystal structure analysis
Search for more papers by this authorClaudio Palomo Prof. Dr.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorMikel Oiarbide Prof. Dr.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorFlavia Dias
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorRosa López Dr.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-212-236
Search for more papers by this authorAnthony Linden Dr.
Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland
crystal structure analysis
Search for more papers by this authorWe thank The University of the Basque Country (EHU/UPV) and Ministerio de Ciencia y Tecnología (Spain) for financial support. A Ramón y Cajal grant to R.L. from Ministerio de Educación Cultura y Deporte and a predoctoral grant to F.D. from EHU/UPV are acknowledged.
Graphical Abstract
Quaternary stereocenters that bear a sulfur substituent can be created with nearly perfect stereocontrol through an intramolecular Michael-type process. Lewis acids (L.A.) accelerate the intramolecular sulfur-atom transfer from the oxazolidine-2-thione functionality to the β carbon atom of the β,β-disubstituted enoyl moiety, whereas the chirality of the oxazolidine-2-thione portion controls reaction stereochemistry (see scheme).
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53889_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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