✦ LIBER ✦

Enantioselective Synthesis of an Allenyl Derivative of Pipecolic Acid

✍ Scribed by Claude Agami; Dominique Bihan; Louis Hamon; Catherine Kadouri-Puchot; Marie Lusinchi

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 205 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199811)1998:11<2461::aid-ejoc2461>3.0.co;2-1

No coin nor oath required. For personal study only.

✦ Synopsis

Addition of a propargylsilane moiety onto chiral cyclic of an allenic amino acid in the acyclic series; however, this isomerization did not take place with the cyclic α-amino ester iminium ions occurs with a high level of stereoselectivity intermolecularly as well as intramolecularly. This operation which was thus obtained with a 55 % ee. AM1 calculations explain the difference of reactivity between cyclic and generates allenic α-amino acids precursors. An isomerization leading to a 1,3-dienyl compound precludes the formation acyclic compounds on a conformational basis.

📜 SIMILAR VOLUMES

ChemInform Abstract: Asymmetric Synthesi

ChemInform Abstract: Asymmetric Synthesis of Unsaturated Pipecolic Acid Derivatives.

✍ C. AGAMI; D. BIHAN; R. MORGENTIN; C. PUCHOT-KADOURI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB

The synthesis of two enantiopure pipecolic acid esters (VI) and (XIII) is reported. Key steps are the intramolecular addition of allyl silane on an iminium double bond, generated via reaction of chiral β-amino alcohols (I) and (VII), with glyoxal (II).

Synthesis of Enantiopure Functionalized

Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid Derived N-Acyliminium Ions

✍ Floris P. J. T. Rutjes; Johan J. N. Veerman; Wim J. N. Meester; Henk Hiemstra; H 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 352 KB 👁 1 views

Asymmetric Syntheses of Enantiopure 4-Su

Asymmetric Syntheses of Enantiopure 4-Substituted Pipecolic Acid Derivatives

✍ Claude Agami; Fabrice Bisaro; Sébastien Comesse; Sébastien Guesné; Catherine Kad 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 263 KB 👁 1 views

ChemInform Abstract: Stereospecific Ally

ChemInform Abstract: Stereospecific Allylation of a Serine-Derived Zinc/Copper Reagent. Synthesis of Substituted Pipecolic Acid Derivatives.

✍ R. F. W. JACKSON; D. TURNER; M. H. BLOCK 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB

Enantioselective synthesis of α-aminopho

Enantioselective synthesis of α-aminophosphonic acid derivatives by hydrogenation

✍ Ute Schmidt; Hans Walter Krause; Günther Oehme; Manfred Michalik; Christine Fisc 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 208 KB

Chiral ␣-aminophosphonic acid derivatives are efficiently synthesized by asymmetric hydrogenation of the prochiral N-acyl-␣,␤-dehydroaminophosphonates. PROPRAPHOS-Rh-catalysts from readily available (S)-and (R)-Propranolol proved to be suitable in the homogenous reaction affording an enantiomeric ex

ChemInform Abstract: Preparation of Enan

ChemInform Abstract: Preparation of Enantiopure 4-Oxygenated Pipecolic Acid Derivatives.

✍ Y. BOUSQUET; P. C. ANDERSON; T. BOGRI; J.-S. DUCEPPE; L. GRENIER; I. GUSE 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB