Literature DB >> 29711355

Solid-State Structural Investigation of an Organolithium (-)-Sparteine Complex: η3 -N-Boc-N-(p-methoxyphenyl)-3-phenylallyllithium⋅(-)-Sparteine.

Daniel J Pippel1, Gerald A Weisenburger1, Scott R Wilson1, Peter Beak1.   

Abstract

A η3 monomeric alkyllithium⋅(-)-sparteine complex has been isolated and characterized in the solid state (see picture). Determination of the absolute configuration of this key intermediate in asymmetric metalation/substitution sequences of N-tert-butoxycarbonyl-N-(p-methoxyphenyl)cinnamylamine allows definitive assignment of the stereochemical course of its electrophile-dependent substitution reactions. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  (−)-sparteine; Asymmetric synthesis; Lithium; Metalations; Structure-activity relationship

Year:  1998        PMID： 29711355     DOI： 10.1002/(SICI)1521-3773(19981002)37:18<2522::AID-ANIE2522>3.0.CO;2-T

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  2 in total

1.  Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.

Authors:  Raphael K Klake; Samantha L Gargaro; Skyler L Gentry; Sharon O Elele; Joshua D Sieber
Journal:  Org Lett       Date:  2019-09-18       Impact factor: 6.005

2.  Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons.

Authors:  Samantha L Gargaro; Raphael K Klake; Kevin L Burns; Sharon O Elele; Skyler L Gentry; Joshua D Sieber
Journal:  Org Lett       Date:  2019-11-26       Impact factor: 6.005
  2 in total

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