Literature DB >> 19950989

A convergent stereoselective synthesis of quinolizidines and indolizidines: chemoselective coupling of 2-hydroxymethyl-substituted allylic silanes with imines.

Dexi Yang1, Glenn C Micalizio.   

Abstract

A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydroxymethyl-substituted allylic silanes and imines is described. Overall, highly substituted heterocycles that contain three stereogenic centers and up to four fused rings can be accessed in two steps from relatively simple coupling partners.

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Year:  2009        PMID： 19950989      PMCID： PMC2818501          DOI： 10.1021/ja908504z

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


  12 in total

1.  Synthesis of organotitanium complexes from alkenes and alkynes and their synthetic applications.

Authors:  F Sato; H Urabe; S Okamoto
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis.

Authors:  O G Kulinkovich; A de Meijere
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

3.  Cyclizations of N-acyliminium ions.

Authors:  Bruce E Maryanoff; Han-Cheng Zhang; Judith H Cohen; Ignatius J Turchi; Cynthia A Maryanoff
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

4.  Molecular Rearrangements in the Construction of Complex Molecules.

Authors:  Larry E Overman
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

5.  A chemistry cascade: from physical organic studies of alkoxy radicals to alkaloid synthesis.

Authors:  Albert Padwa
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

Review 6.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2007-01-03       Impact factor: 13.423

7.  Asymmetric synthesis of alpha-substituted beta-amino ketones from sulfinimines (N-sulfinyl imines). synthesis of the indolizidine alkaloid (-)-223A.

Authors:  Franklin A Davis; Bin Yang
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Indolizidine 239Q and quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus).

Authors:  John W Daly; H Martin Garraffo; Thomas F Spande; Herman J C Yeh; Paola M Peltzer; Pedro M Cacivio; J Diego Baldo; Julián Faivovich
Journal:  Toxicon       Date:  2008-09-20       Impact factor: 3.033

9.  Aliphatic imines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)4/n-BuLi.

Authors:  Michael A Tarselli; Glenn C Micalizio
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

10.  Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.

Authors:  Masayuki Takahashi; Martin McLaughlin; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  12 in total

1.  Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

Authors:  Ming Z Chen; Martin McLaughlin; Masayuki Takahashi; Michael A Tarselli; Dexi Yang; Shuhei Umemura; Glenn C Micalizio
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.

Authors:  Hsin-Chun Chiu; Xin Yi See; Ian A Tonks
Journal:  ACS Catal       Date:  2018-11-29       Impact factor: 13.084

3.  Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors:  Glenn C Micalizio; Sarah B Hale
Journal:  Acc Chem Res       Date:  2015-02-10       Impact factor: 22.384

4.  Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; Patrick Porubsky; Farman Ullah; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-02-06       Impact factor: 3.784

5.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

6.  A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.

Authors:  Zachary A Shalit; Glenn C Micalizio
Journal:  ARKIVOC       Date:  2018-03-28       Impact factor: 1.140

7.  Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

Authors:  Dexi Yang; Justin K Belardi; Glenn C Micalizio
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

8.  Convergent and stereodivergent synthesis of complex 1-aza-7-oxabicyclo[2.2.1]heptanes.

Authors:  Dexi Yang; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2011-05-23       Impact factor: 15.419

9.  Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.

Authors:  Yongho Park; Corinna S Schindler; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-11-03       Impact factor: 15.419

10.  The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Authors:  Allan U Barlan; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457
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