Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 5
Submit an article Journal homepage
853
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Modification of the Titanium(IV) Isopropoxide Reductive Amination Reaction: Application to Solid Phase Synthesis

John C. DiCesare Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK, USACorrespondencejohn‐[email protected]
,
Celesta E. White Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK, USA
,
Wendy E. Rasmussen Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK, USA
,
Bryan M. White Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK, USA
,
Charles B. McComas Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK, USA
&
Laura E. Craft Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK, USA
Pages 663-668 | Received 24 Oct 2004, Published online: 20 Aug 2006

References

  • Borch , R. F. and Durst , H. D. 1969 . Lithium cyanohydridoborate, a versatile new reagent . J. Amer. Chem. Soc. , 91 ( 14 ) : 3996 – 3997 .
  • Borch , R. F. , Bernstein , M. D. and Durst , H. D. 1971 . Cyanohydridoborate anion as a selective reducing agent . J. Amer. Chem. Soc. , 93 ( 12 ) : 2897 – 2904 .
  • Barney , C. L. , Huber , E. W. and McCarthy , J. R. 1990 . A conveninent synthesis of hindered amines and a‐trifluoromethylamines from ketones . Tetrahedron Lett. , 31 ( 39 ) : 5547 – 5550 .
  • Mattson , R. J. , Pham , K. M. , Leuck , D. J. and Cowen , K. A. 1990 . An improved method for reductive alkylation of amines using titanium(IV) isopropoxide and sodium cyanoborohydridge . J. Org. Chem. , 55 ( 8 ) : 2552 – 2554 .
  • Aoki , Y. and Kobayashi , S. 1999 . Development of a reductive alkylation method using p‐benzyloxybenzylamine (BOBA) resin for the synthesis of N‐alkylated amides . J. Comb. Chem. , 1 ( 5 ) : 371 – 372 .
  • Szardenings , A. K. , Burkoth , T. S. , Look , G. C. and Campbell , D. A. 1996 . A reductive alkylation procedure applicable to both solution‐ and solid‐phase syntheses of secondary amines . J. Org. Chem. , 61 ( 19 ) : 6720 – 6722 .
  • Gordon , D. W. and Steele , J. 1995 . Reductive alkylation on a solid phase: synthesis of a piperazinedione combinatorial library . Bioorg. Med. Chem. Lett. , 5 ( 1 ) : 47 – 50 .
  • DiCesare , J. C. , McComas , C. B. , Thomas , J. and Carroll , F. I. Modification of the titanium isopropoxide catalyzed reductive amination reaction and its application to solid phase synthesis . Abstract of Papers, 211th National Meeting . March 24–28 1996 , New Orleans, LA. Washington, DC : American Chemical Society . ORGN‐91
  • Bhattacharyya , S. 1995 . Reductive alkylation of dimethylamine using titanium(IV) isopropoxide and sodium borohydride: an efficient, safe, and convenient method for the synthesis of N,N‐dimethylated tertiary amines . J. Org. Chem. , 60 ( 15 ) : 4928 – 4929 .
  • Abdel‐Magid , A. F. , Carson , K. G. , Harris , B. D. , Maryanoff , C. A. and Shah , R. D. 1996 . Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures . J. Org. Chem. , 61 ( 11 ) : 3849 – 3862 .
  • Frenette , R. and Friesen , R. W. 1994 . Biaryl synthesis via Suzuki coupling on a solid support . Tetrahedron Lett. , 35 ( 49 ) : 9177 – 9180 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.