Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles
- PMID: 12904019
- DOI: 10.1021/ja035001g
Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles
Abstract
A highly practical method for the enantioselective allylation of acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in >/=98% ee.
Similar articles
-
Enantioselective allylation of ketone-derived benzoylhydrazones: practical synthesis of tertiary carbinamines.J Am Chem Soc. 2004 May 12;126(18):5686-7. doi: 10.1021/ja0486418. J Am Chem Soc. 2004. PMID: 15125659
-
Enantioselective imidazole-directed allylation of aldimines and ketimines.Org Lett. 2007 Aug 30;9(18):3699-701. doi: 10.1021/ol701723w. Epub 2007 Aug 8. Org Lett. 2007. PMID: 17685538
-
A new silicon lewis acid for highly enantioselective mannich reactions of aliphatic ketone-derived hydrazones.J Am Chem Soc. 2008 May 28;130(21):6676-7. doi: 10.1021/ja800830h. Epub 2008 Apr 30. J Am Chem Soc. 2008. PMID: 18444641
-
N-acylhydrazones as versatile electrophiles for the synthesis of nitrogen-containing compounds.Angew Chem Int Ed Engl. 2005 Aug 19;44(33):5176-86. doi: 10.1002/anie.200500691. Angew Chem Int Ed Engl. 2005. PMID: 16059954 Review.
-
Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions.Chem Rev. 2008 Aug;108(8):2796-823. doi: 10.1021/cr0683515. Epub 2008 Aug 1. Chem Rev. 2008. PMID: 18671436 Review. No abstract available.
Cited by
-
Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.Org Lett. 2009 Oct 1;11(19):4362-5. doi: 10.1021/ol901692n. Org Lett. 2009. PMID: 19775184 Free PMC article.
-
Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.J Org Chem. 2010 Dec 3;75(23):8048-59. doi: 10.1021/jo101535d. Epub 2010 Nov 11. J Org Chem. 2010. PMID: 21069994 Free PMC article.
-
Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4701-6. doi: 10.1002/anie.201600546. Epub 2016 Mar 9. Angew Chem Int Ed Engl. 2016. PMID: 26961497 Free PMC article.
-
Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs.Curr Org Chem. 2015;19(10):871-885. doi: 10.2174/1385272819666150119225149. Curr Org Chem. 2015. PMID: 27182194 Free PMC article.
-
Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.Angew Chem Int Ed Engl. 2009;48(20):3648-52. doi: 10.1002/anie.200900236. Angew Chem Int Ed Engl. 2009. PMID: 19360820 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources