New Efficient Route to the Synthesis of Enantiopure (+) and (−) Bicyclo[2.2.1]heptan‐syn‐2,7‐diol using Lipase‐Catalyzed Transesterifications

References

• Blaser , H. U. 1992 . The chiral pool as a source of enantioselective catalysts and auxiliaries . Chem. Rev. , 92 : 935 – 952 .
   Web of Science ®Google Scholar
• Schmidt , B. and Seebach , D. 1991 . Catalytic and stoichiometric enantioselective addition of diethylzinc to aldehydes using a novel chiral spirotitanate . Angew. Chem., Int. Ed. Engl. , 30 : 99 – 101 .
   Google Scholar
• Schmidt , B. and Seebach , D. 1991 . 2,2‐Dimethyl‐α,α,α′,α′‐tetrakis(β‐naphthyl)‐1,3‐dioxolan‐4,5‐dimethanol (DINOL) for the titanate‐mediated enantioselective addition of diethylzinc to aldehydes . Angew. Chem., Int. Ed. Engl. , 30 : 1321 – 1323 .
   Google Scholar
• Seebach , D. , Plattner , D. A. , Beck , A. K. , Wang , Y. M. and Hunziker , D. 1992 . On the mechanisms of enantioselective reactions using α,α,α′,α′‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol (TADDOL)–derived titanates: Differences between C2‐ and C1‐symmetrical TADDOLs—facts, implications and generalizations . Helv. Chim. Acta , 75 : 2171
   Google Scholar
• Weber , B. and Seebach , D. 1994 . Ti‐TADDOLate‐catalyzed, highly enantioselective addition of alkyl‐ and aryl‐titanum derivatives to aldehydes . Tetrahedron , 50 : 7473 – 7484 .
   Google Scholar
• Seebach , D. , Beck , A. K. , Schmidt , B. and Wang , Y. M. 1994 . Enantio‐ and diastereoselective titanium‐TADDOLate‐catalyzed addition of diethyl and bis(3‐buten‐1‐yl) zinc to aldehydes a full account with preparative details . Tetrahedron , 50 : 4363 – 4384 .
   Google Scholar
• Ito , Y. N. , Ariza , X. , Beck , A. K. , Bohac , A. , Ganter , C. , Gawley , R. E. , Kuhnle , F. N. M. , Tuleja , J. , Wang , Y. M. and Seebach , D. 1994 . Preparation and structural analysis of several new α,α,α′,α′‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols (TADDOL's) and TADDOL analogs, their evaluation as titanium ligands in the enantioselective addition of methyltitanium and diethylzinc reagents to benzaldehyde, and refinement of the mechanistic hypothesis . Helv. Chim. Acta , 77 : 2071
   Google Scholar
• Kagan , H. B. and Riant , O. 1992 . Catalytic asymmetric Diels–Alder reactions . Chem. Rev. , 92 : 1007 – 1019 .
   Web of Science ®Google Scholar
• Mikami , K. and Shimizu , M. 1992 . Asymmetric ene reactions in organic synthesis . Chem. Rev. , 92 : 1021 – 1050 .
   Web of Science ®Google Scholar
• Minamikawa , H. , Hayakawa , S. , Yamada , T. , Iwasawa , N. and Narasata , N. 1988 . Asymmetric hydrocyanation of aldehydes using chiral titanium reagents . Bull. Chem. Soc. Jpn. , 61 : 4379
   Google Scholar
• Naemura , K. , Takahashi , N. , Tanaka , S. , Ueno , M. and Chikamatsu , H. 1990 . Enzyme‐catalyzed enantioselective and regioselective hydrolyses of (2RS, 7SR)‐2,7‐diacetoxybicyclo[2.2.1]heptane and (2RS, 7RS)‐2,7‐diacetoxybicyclo [2.2.1]heptane . Bull. Chem. Soc. Jpn. , 63 : 1010
   Google Scholar
• Costa , V. E. U. , Alifantes , J. and Martins , J. E.D. 1998 . Evaluation of lipase from Candida rugosa in the resolution of endo‐(±)‐1,8,9,10,11,11‐ hexacloropentacyclo [6.2.1.13,6.02,7.05,9] dodecan‐4‐alcohol . Tetrahedron: Asymmetry , 9 : 2579 – 2585 .
   Google Scholar
• Costa , V. E. U. , Lapis , A. A. M. , Kreutz , O. C. and Pohlmann , A. R. 2001 . An efficient synthesis of enantiopure (+) and (−)‐3‐exo‐amino‐7,7‐dimethoxynorbornan‐2‐exo‐ols . Tetrahedron: Asymmetry , 12 : 557 – 561 .
   Google Scholar
• Costa , V. E. U. and Morisso , F. D. P. 2001 . Kinetic resolution of (±)‐5‐bromo‐12‐oxa‐pentacyuclo[6.2.1.16,9.02,7.02,10]dodeca‐4‐ene‐3‐endo‐ol and (±)‐5‐bromo‐13‐oxa‐pentacyclo[6.2.2.16,9.02,7.02,10]trideca‐4‐ene‐3‐endo‐ol via pseudomonas‐mediated lipase‐catalyzed transesterification . Tetrahedron: Asymmetry , 12 : 2641 – 2647 .
   Google Scholar
• Costa , V. E. U. , Alifantes , J. and Nichele , A. G. 2002 . Asymmetric synthesis of half‐cage alcohol compounds . Tetrahedron: Asymmetry , 13 : 2019 – 2024 .
   Google Scholar
• Costa , V. E. U. , Alifantes , J. , Pohlmann , A. R. and Martins , J. E. D. 2003 . Study of the kinetic resolution of (±)‐10‐exo‐hydroxy‐pentacyclo[6.2.1.13,6.02,7.05,9]dodeca‐4‐one by lipase catalysis and the intramolecular racemization of the pure enantiomer by thermal dyotropic reaction . Tetrahedron: Asymmetry , 14 : 683 – 688 .
   Google Scholar
• Costa , V. E. U. , Pohlmann , A. R. and de Sordi , M. L.T. 2004 . Evaluation of lipases in the desymmetrization of meso‐exo‐3,5‐dihydroxymethylenetricyclo[5.2.1.02,6]decane and synthesis of chiral derivatives . J. Bras. Chem. Soc. , 15 : 22 – 27 .
   Google Scholar
• Costa , V. E. U. and Oliveira , L. F. 2004 . An efficient synthesis of enantiopure (+) and (−) syn‐1,3‐amino alcohols with norbornane framework and their application in chiral addition of ZnEt2 to benzaldehyde . Tetrahedron: Asymmetry , 15 : 2583 – 2590 .
   Google Scholar
• Pilli , R. A. , Costa , V. E. U. , Lapis , A. A. M. , Martins , J. E. D. and Fátima , A. 2005 . Asymmetric reduction of prochiral ketones using in situ generated oxazaborolidina derived from (1S,2S,3R,4R)‐3‐amino‐7,7‐dimethoxynorbornan‐2‐ol: An efficient synthesis of enantiopure (R)‐tomoxetine . Tetrahedron Lett. , 46 : 495 – 498 .
   Google Scholar
• Berger , B. , Rabiller , C. G. , Konigsberger , K. , Gringl , H. and Faber , K. 1990 . Enzymatic acylation using acid anhydrides: Crucial removal of acid . Tetrahedron: Asymmetry , 1 : 541 – 546 .
   Google Scholar
• Kotsuki , H. , Kataoka , M. and Nishizawa , H. 1993 . High pressure‐promoted uncatalyzed hydrolysis of epoxides . Tetrahedron Lett. , 34 : 4031 – 4034 .
   Google Scholar