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Asymmetric Synthesis and Highly Diastereoselective ortho-Lithiation of Ferrocenyl Sulfoxides. Application to the Synthesis of Ferrocenyl Derivatives with Planar Chirality

✍ Scribed by Dr. François Rebière; Dr. Olivier Riant; Dr. Louis Ricard; Prof. Dr. Henri B. Kagan

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
366 KB
Volume
32
Category
Article
ISSN
0044-8249

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✦ Synopsis

2, which may be rationalized in a straightforward the situation here is more complex. With non-symmetric phosphinoaryldihydrooxazoles, two diastereomeric ally1 palladium intermediates must be considered, and in addition to steric interactions, electronic effects may play a role as well (differing trans-influence of the coordinating N and P atom; see, e.g., ref. [Id]).

Further studies, exploring the scope of these promising catalysts and the mechanism of enantioselection, are in progress. We are also examining the use of phosphinoaryldihydrooxazoles in other metal-catalyzed reactions.

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Diastereoselective 1,2-Addition of Organ
Diastereoselective 1,2-Addition of Organometallic Reagents to Chiral Formylferrocenes Leading to Enantiomerically Pure Ferrocenyl Amino Alcohols: Application to Asymmetric Dialkylzinc Addition to Aldehydes and Synthesis of Optically Active 1,2-Homodisubstituted Ferrocenes
✍ Shin-ichi Fukuzawa; Daisuke Tsuchiya; Kae Sasamoto; Kohki Hirano; Makoto Ohtaguc 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 341 KB 👁 2 views

The chiral formylferrocenes 2-5 have been readily prepared in good yields by ortho-lithiation of the TMS-blocked orunblocked aminoferrocenes and subsequent reaction with DMF. The stereochemistry of the reaction of 2 with organometallic reagents has been examined. Reactions of 2 with Grignard and org