Literature DB >> 12358529

A readily-accessible (+)-sparteine surrogate.

Michael J Dearden1, Catherine R Firkin, Jean-Paul R Hermet, Peter O'Brien.   

Abstract

A "(+)-sparteine-like" chiral diamine, readily synthesized in three steps from (-)-cytisine, has been evaluated in four different asymmetric transformations; in each case, selectivity in an enantiocomplementary fashion to (-)-sparteine was observed.

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Year:  2002        PMID： 12358529     DOI： 10.1021/ja027774v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

1.  Palladium-catalyzed enantioselective oxidation of chiral secondary alcohols: access to both enantiomeric series.

Authors:  David C Ebner; Raissa M Trend; Cédric Genet; Matthew J McGrath; Peter O'Brien; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Assignment and stereocontrol of hibarimicin atropoisomers.

Authors:  Ian M Romaine; Jonathan E Hempel; Ganesh Shanmugam; Hiroshi Hori; Yasuhiro Igarashi; Prasad L Polavarapu; Gary A Sulikowski
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

3.  Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy.

Authors:  Ramesh Rasappan; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-07-27       Impact factor: 24.427

4.  Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.

Authors:  Bo Qu; Hari P R Mangunuru; Sergei Tcyrulnikov; Daniel Rivalti; Olga V Zatolochnaya; Dmitry Kurouski; Suttipol Radomkit; Soumik Biswas; Shuklendu Karyakarte; Keith R Fandrick; Joshua D Sieber; Sonia Rodriguez; Jean-Nicolas Desrosiers; Nizar Haddad; Keith McKellop; Scott Pennino; Heewon Lee; Nathan K Yee; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2018-02-20       Impact factor: 6.005

5.  Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines.

Authors:  Timothy K Beng; Robert E Gawley
Journal:  Org Lett       Date:  2010-12-21       Impact factor: 6.005

6.  Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.

Authors:  Xi-Jie Dai; Oliver D Engl; Thierry León; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

7.  Asymmetric hydrosilylation of ketones catalyzed by complexes formed from trans-diaminocyclohexane-based diamines and diethylzinc.

Authors:  Jadwiga Gajewy; Jacek Gawronski; Marcin Kwit
Journal:  Monatsh Chem       Date:  2012-04-18       Impact factor: 1.451

8.  Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization.

Authors:  Andrew R Germain; Daniel M Bruggemeyer; Jianglong Zhu; Cedric Genet; Peter O'Brien; John A Porco
Journal:  J Org Chem       Date:  2011-03-14       Impact factor: 4.354

9.  Structural features and reactivity of (sparteine)PdCl2: a model for selectivity in the oxidative kinetic resolution of secondary alcohols.

Authors:  Raissa M Trend; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

Review 10.  Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

Authors:  Andrew F Zahrt; Soumitra V Athavale; Scott E Denmark
Journal:  Chem Rev       Date:  2019-12-30       Impact factor: 60.622
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