Synthetically Useful Intermediates by Diazosulfone and Sulfonate C–H Insertion

REFERENCES

• John , J. P. ; Novikov , A. V. Selective formation of six-membered cyclic sulfones and sulfonates by C–H insertion . Org. Lett. 2007 , 9 , 61 – 63 .
   PubMed Web of Science ®Google Scholar
• Wolckenhauer , S.A. ; Devlin , A. S. ; Du Bois , J. δ-Sultone formation through Rh-catalyzed C–H insertion . Org. Lett. 2007 , 9 , 4363 – 4366 .
   PubMed Web of Science ®Google Scholar
• Flynn , C. J. ; Elcoate , C.J. ; Lawrence , S. E. ; Maguire , A. R. Highly enantioselective intramolecular copper-catalyzed C–H insertion reactions of α-diazosulfones . J. Am. Chem. Soc. 2010 , 108 , 7686 – 7693 .
   Google Scholar
• Taber , D. F. ; Ruckle Jr. , R. E. Cyclopentane construction by dirhodium tetraacetate-mediated intramolecular C–H insertion: Steric and electronic effects . J. Am. Chem. Soc. 1986 , 108 , 7686 – 7693 .
   PubMed Web of Science ®Google Scholar
• Doyle , M. P. ; Westrum , L. J. ; Wolthuis , W. N. E. ; See , M. M. ; Boone , W. P. ; Bagheri , V. ; Pearson , M. M. Electronic and steric control in carbon-hydrogen insertion reactions of diazoacetoacetates catalyzed by dirhodium(II) carboxylates and carboxamides . J. Am. Chem. Soc. 1993 , 115 , 958 – 964 .
   Web of Science ®Google Scholar
• Jungong , C. J. ; John , J. P. ; Novikov , A. V. Formation of six- versus five-membered cyclic sulfones by C–H insertion . Tetrahedron Lett. 2009 , 50 , 1954 – 1957 .
   PubMed Web of Science ®Google Scholar
• Bequette , J. P. ; Jungong , C. J. ; Novikov , A. V. Synthesis of bakuchiol using C–H insertion to install the quaternary center . Tetrahedron Lett. 2009 , 50 , 6963 – 6964 .
   PubMed Web of Science ®Google Scholar
• Schurig , V. ; Leyrer , U. ; Wistuba , D. Simple access to highly enantiomerically enriched (S)-3-methyl-1-pentanol, (S)-3-methyl-1-pentene, (2R,3S)-2-deuterio-3-methyl-1-pentanol, and (2S,3S)-3-methyl-2-pentanol from natural (L)-isoleucine . J. Org. Chem. 1986 , 51 , 242 – 245 .
   Web of Science ®Google Scholar
• Jungong , C. J. ; John , J. P. ; Bequette , J. P. ; Novikov , A. V. Synthetically useful transformations of δ-sultones and thiane-1,1-dioxides obtained by C–H insertion . Heterocycles 2009 , 78 , 2531 – 2539 .
   Web of Science ®Google Scholar
• Chen , Y.-H. ; McDonald , F. E. New chiral synthons for efficient introduction of bispropionates via stereospecific Oxonia−Cope rearrangements . J. Am. Chem. Soc. 2006 , 128 , 4568 – 4569 .
   PubMed Web of Science ®Google Scholar
• Myers , A. G. ; Yang , B. H. ; Chen , H. ; McKinstry , L. ; Kopecky , D. J. ; Gleason , J. L. Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones . J. Am. Chem. Soc. 1997 , 119 , 6496 – 6511 .
   Web of Science ®Google Scholar
• Wang , A. ; Fraga , R. P. A. ; Hormann , E. ; Pfaltz , A. Iridium-catalyzed asymmetric hydrogenation of unfunctionalized, trialkyl-substituted olefins . Chem. Asian J. 2011 , 6 , 599 – 606 .
   PubMed Web of Science ®Google Scholar
• Mikolajczyk , M. ; Perlikowska , W. ; Omelanczuk , J. Synthesis of (+)-neomenthanethiol and some of its derivatives: A new example of asymmetric induction in the sulfoxide synthesis . Synthesis 1987 , 1009 – 1012 .
   Web of Science ®Google Scholar