Synthesis of a Bicyclic Diamine Derived from Kemp's Acid

REFERENCES

• Kemp , D. S. ; Petrakis , K. S. Synthesis and conformational analysis of cis,cis-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid . J. Org. Chem. 1981 , 46 , 5140 – 5143 .
   Web of Science ®Google Scholar
• Bach , T. ; Bergmann , H. ; Grosch , B. ; Harms , K. ; Herdtweck , E. Synthesis of enantiomerically pure 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-ones as chiral host compounds for enantioselective photochemical reactions in solution . Synthesis 2001 , 1395 – 1405 .
   Google Scholar
• Grosch , B. ; Orlebar , C. N. ; Herdtweck , E. ; Massa , W. ; Bach , T. Highly enantioselective Diels–Alder reaction of a photochemically generated o-quinodimethane with olefins. Angew. Chem. 2003, 115, 3822–3824; Angew. Chem Int. Ed. 2003, 32, 3693–3696.
   Google Scholar
• Bauer , A. ; Westkämper , F. ; Grimme , S. ; Bach , T. Catalytic enantioselective reactions driven by photoinduced electron transfer . Nature 2005 , 436 , 1139 – 1140 .
   PubMed Web of Science ®Google Scholar
• Kocis , P. ; Issakova , O. ; Sepetov , N. F. ; Lebl , M. Kemp's triacid scaffolding for the synthesis of combinatorial nonpeptide uncoded libraries . Tetrahedron Lett. 1995 , 36 , 6623 – 6626 .
   Web of Science ®Google Scholar
• Stack , J. G. ; Curran , D. P. ; Geib , S. V. ; Rebek , J. Jr. ; Ballester , P. A new chiral auxiliary for asymmetric thermal reactions: High stereocontrol in radical addition, allylation, and annulation reactions . J. Am. Chem. Soc. 1992 , 114 , 7007 – 7018 .
   Google Scholar
• Jeong , K.-S. ; Parris , K. ; Ballester , P. ; Rebek , J. Jr. New chiral auxiliaries for enolate alkylations . Angew. Chem. 1990 , 102 , 550 – 551 ; Angew. Chem. Int. Ed. 1990, 29, 555–556 .
   Google Scholar
• Svoboda , J. ; König , B. Templated photochemistry: Towards catalysts enhancing the efficiency and selectivity of photoreactions in homogeneous solutions . Chem. Rev. 2006 , 106 , 5413 – 5430 .
   Google Scholar
• Yanagisawa , A. ; Kikuchi , T. ; Watanabe , T. ; Yamamoto , H. Enantioselective protonation of lithium enolates with chiral imides possessing a chiral amide . Bull. Chem. Soc. Jpn. 1999 , 72 , 2337 – 2343 .
   Google Scholar
• Yanagisawa , A. ; Watanabe , T. ; Kikuchi , T. ; Yamamoto , H. Catalytic enantioselective protonation of lithium enolates with chiral imides . J. Org. Chem. 2000 , 65 , 2979 – 2983 .
   Google Scholar
• Askew , B. ; Ballester , P. ; Buhr , C. ; Jeong , K. S. ; Jones , S. ; Parris , K. ; Williams , K. ; Rebek , J. Jr. Molecular recognition with convergent functional groups, 6: Synthetic and structural studies with a model receptor for nucleic acid components . J. Am. Chem. Soc. 1989 , 111 , 1082 – 1090 .
   Web of Science ®Google Scholar
• Castellano , R. K. ; Gramlich , V. ; Diederich , F. Rebek imides and their adenine complexes: Preferences for Hoogsteen binding in the solid state and in solution . Chem. Eur. J. 2002 , 8 , 118 – 129 .
   Google Scholar
• Kirby , A. J. ; Komarov , I. V. ; Feeder , N. Synthesis, structure, and reactions of the most twisted amide . J. Chem. Soc., Perkin Trans. 2 2001 , 522 – 529 .
   Google Scholar
• Rebek , J. Jr. ; Askew , B. ; Kolloran , M. ; Nemeth , D. ; Lin , F.-T. Convergent functional groups, 3: A molecular cleft recognizes substrates of complementary size, shape, and functionality . J. Am. Chem. Soc. 1987 , 109 , 2426 – 2431 .
   Web of Science ®Google Scholar
• Besidsky , Y. ; Luthman , K. ; Claesson , A. ; Csöregh , I. ; Hacksell , U. Synthesis and reactivity of 6-carbaomyl-5-phenyl-2,3,5,6-tetrahydro-1H-1,4-ethanobenzo[f]quinoline: X-ray molecular structure of (4aR*,5S*,6R*,10bR*)-5-phenyl-2,3,4a,5,6,10b-hexahydro-1H-1,4-ethanobenzo[f]quinolin-6-yl acetate . J. Chem. Soc., Perkin Trans. 1 1995 , 475 – 480 .
   Google Scholar
• Epstein , J. W. ; Brabander , H. J. ; Fanshawe , W. J. ; Hofmann , C. M. ; McKenzie , T. C. ; Safir , S. R. ; Osterberg , A. C. ; Cosulich , D. B. ; Lovell , F. M. l-Aryl-3-azabicyclo[3.l.0]hexanes, a new series of nonnarcotic analgesic agents . J. Med. Chem. 1981 , 24 , 481 – 490 .
   PubMedGoogle Scholar
• Gawley , R. E. ; Chemburkar , S. R. ; Smith , A. L. ; Anklekar , T. V. (R,R)-1,3-Dibenzylisoindoline: A new C2-symmetric secondary amine, by stereoselective and regioselective α, α′-dialkylation of isoindoline, and an improved procedure for the preparation of isoindoline. J. Org. Chem. 1988, 53, 5381–5383.
   Google Scholar