Literature DB >> 22609828

Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes.

Varinder K Aggarwal1, Liam T Ball, Simon Carobene, Rickki L Connelly, Matthew J Hesse, Benjamin M Partridge, Philippe Roth, Stephen P Thomas, Matthew P Webster.   

Abstract

The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

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Year:  2012        PMID: 22609828     DOI: 10.1039/c2cc32176a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  5 in total

1.  Enantioselective synthesis of (R)-tolterodine using lithiation/borylation-protodeboronation methodology.

Authors:  Stefan Roesner; Varinder K Aggarwal
Journal:  Can J Chem       Date:  2012-11       Impact factor: 1.118

2.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

3.  Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes.

Authors:  Suppachai Krajangsri; Haibo Wu; Jianguo Liu; Wangchuk Rabten; Thishana Singh; Pher G Andersson
Journal:  Chem Sci       Date:  2019-02-04       Impact factor: 9.825

Review 4.  The pinene scaffold: its occurrence, chemistry, synthetic utility, and pharmacological importance.

Authors:  Rogers J Nyamwihura; Ifedayo Victor Ogungbe
Journal:  RSC Adv       Date:  2022-04-12       Impact factor: 3.361

5.  Enantioselective installation of adjacent tertiary benzylic stereocentres using lithiation-borylation-protodeboronation methodology. Application to the synthesis of bifluranol and fluorohexestrol.

Authors:  Stefan Roesner; Daniel J Blair; Varinder K Aggarwal
Journal:  Chem Sci       Date:  2015-04-28       Impact factor: 9.825

  5 in total

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