O,O-acetal formation of exo-annelated octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol with lactic acid and phenyllactic acid derivatives

Monatshefte fur Chemie

Volumn 129, Issue 3, 1998, Pages 281-289

  Girreser, Ulrich ^a,b   Haberhauer, Georg ^a,c   Noe, Christian R ^a  

^a GOETHE UNIVERSITY   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

^c ARC SEIBERSDORF RESEARCH GMBH   (Austria)

Author keywords

Acetalization; Enantiomeric excess; Enantiomeric selectivity; Lactamides; Lactic esters

Indexed keywords

EID: 0040844791     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/PL00000086     Document Type: Article

References (30)

1. Noe CR (1982) Chem Ber 115: 1576
2. Noe CR, Knollmüller M, Göstl G, Steinbauer BG, Völlenkle H (1986) Chem Ber 119: 729
3. Noe CR, Knollmüller M, Ziebarth-Schroth I, Letschnig M (1996) Liebigs Ann Chem 1009; for reviews of recent developments in the understanding of the anomeric and exo-anomeric effect: Juaristi E, Cuevas G (1992) Tetrahedron 48: 5019; Thatcher GJR (1993) Anomeric Effect and Associated Stereoelectronic Effects ACS Symp Ser 539: 6; Deslongchamps P (1993) ibid 26; Kirby AJ, Williams DH (1993) ibid 55
4. Noe CR, Knollmüller M, Ziebarth-Schroth I, Letschnig M (1996) Liebigs Ann Chem 1009; for reviews of recent developments in the understanding of the anomeric and exo-anomeric effect: Juaristi E, Cuevas G (1992) Tetrahedron 48: 5019; Thatcher GJR (1993) Anomeric Effect and Associated Stereoelectronic Effects ACS Symp Ser 539: 6; Deslongchamps P (1993) ibid 26; Kirby AJ, Williams DH (1993) ibid 55
5. Noe CR, Knollmüller M, Ziebarth-Schroth I, Letschnig M (1996) Liebigs Ann Chem 1009; for reviews of recent developments in the understanding of the anomeric and exo-anomeric effect: Juaristi E, Cuevas G (1992) Tetrahedron 48: 5019; Thatcher GJR (1993) Anomeric Effect and Associated Stereoelectronic Effects ACS Symp Ser 539: 6; Deslongchamps P (1993) ibid 26; Kirby AJ, Williams DH (1993) ibid 55
6. Noe CR, Knollmüller M, Ziebarth-Schroth I, Letschnig M (1996) Liebigs Ann Chem 1009; for reviews of recent developments in the understanding of the anomeric and exo-anomeric effect: Juaristi E, Cuevas G (1992) Tetrahedron 48: 5019; Thatcher GJR (1993) Anomeric Effect and Associated Stereoelectronic Effects ACS Symp Ser 539: 6; Deslongchamps P (1993) ibid 26; Kirby AJ, Williams DH (1993) ibid 55
7. Noe CR, Knollmüller M, Ziebarth-Schroth I, Letschnig M (1996) Liebigs Ann Chem 1009; for reviews of recent developments in the understanding of the anomeric and exo-anomeric effect: Juaristi E, Cuevas G (1992) Tetrahedron 48: 5019; Thatcher GJR (1993) Anomeric Effect and Associated Stereoelectronic Effects ACS Symp Ser 539: 6; Deslongchamps P (1993) ibid 26; Kirby AJ, Williams DH (1993) ibid 55
8. a) Noe CR (1982) Chem Ber 115: 1591;
9. b) Noe CR, Knollmüller M, Wagner E, Völlenkle H (1985) Chem Ber 118: 1733;
10. c) Knollmüller M, Noe CR, Oberhauser B (1986) Monatsh Chem 117: 407;
11. d) Noe CR, Knollmüller M, Göstl G, Oberhauser B, Völlenkle H (1987) Angew Chem 99: 467; Angew Chem Int Ed Engl 26: 442;
12. d) Noe CR, Knollmüller M, Göstl G, Oberhauser B, Völlenkle H (1987) Angew Chem 99: 467; Angew Chem Int Ed Engl 26: 442;
13. e) Noe CR, Knollmüller M, Miculka C, Dungler K, Wagner E, Ettmayer P (1994) Chem Ber 127: 887
14. Lefker BA, Hada WA, McGarry PJ (1994) Tetrahedron Lett 35: 5205 and references therein; recent examples in the evaluation of new analytical methods for the determination of the absolute configuration of functionalized alcohols by diastereomer formation: Trujillo M, Morales EQ, Vázquez JT (1994) J Org Chem 59: 6637; Hammerschmidt F, Li Y-F (1994) Tetrahedron 50: 10253
15. Lefker BA, Hada WA, McGarry PJ (1994) Tetrahedron Lett 35: 5205 and references therein; recent examples in the evaluation of new analytical methods for the determination of the absolute configuration of functionalized alcohols by diastereomer formation: Trujillo M, Morales EQ, Vázquez JT (1994) J Org Chem 59: 6637; Hammerschmidt F, Li Y-F (1994) Tetrahedron 50: 10253
16. Lefker BA, Hada WA, McGarry PJ (1994) Tetrahedron Lett 35: 5205 and references therein; recent examples in the evaluation of new analytical methods for the determination of the absolute configuration of functionalized alcohols by diastereomer formation: Trujillo M, Morales EQ, Vázquez JT (1994) J Org Chem 59: 6637; Hammerschmidt F, Li Y-F (1994) Tetrahedron 50: 10253
17. Juaristi E, Tapia J, Mendez R (1986) Tetrahedron 42: 1253; Juaristi E, Gonzalez EA, Pinto B, Johnston BD, Nagelkerke R (1989) J Am Chem Soc 111: 6745; Tschierske C, Köhler H, Zaschke H, Kleinpeter E (1989) Tetrahedron 45: 6987; Krol MC, Huige CJM, Altona C (1990) J Comp Chem 11: 765
18. Juaristi E, Tapia J, Mendez R (1986) Tetrahedron 42: 1253; Juaristi E, Gonzalez EA, Pinto B, Johnston BD, Nagelkerke R (1989) J Am Chem Soc 111: 6745; Tschierske C, Köhler H, Zaschke H, Kleinpeter E (1989) Tetrahedron 45: 6987; Krol MC, Huige CJM, Altona C (1990) J Comp Chem 11: 765
19. Juaristi E, Tapia J, Mendez R (1986) Tetrahedron 42: 1253; Juaristi E, Gonzalez EA, Pinto B, Johnston BD, Nagelkerke R (1989) J Am Chem Soc 111: 6745; Tschierske C, Köhler H, Zaschke H, Kleinpeter E (1989) Tetrahedron 45: 6987; Krol MC, Huige CJM, Altona C (1990) J Comp Chem 11: 765
20. Juaristi E, Tapia J, Mendez R (1986) Tetrahedron 42: 1253; Juaristi E, Gonzalez EA, Pinto B, Johnston BD, Nagelkerke R (1989) J Am Chem Soc 111: 6745; Tschierske C, Köhler H, Zaschke H, Kleinpeter E (1989) Tetrahedron 45: 6987; Krol MC, Huige CJM, Altona C (1990) J Comp Chem 11: 765
21. The effects observed in the acetalizations of monosubstituted α-hydroxy carboxamides will be published in due course: Girreser U, Noe CR, Haberhauer G, Mereiter K (in preparation); for the synthesis, see: Girreser U, Noe CR (1995) Synthesis 1123
22. The effects observed in the acetalizations of monosubstituted α-hydroxy carboxamides will be published in due course: Girreser U, Noe CR, Haberhauer G, Mereiter K (in preparation); for the synthesis, see: Girreser U, Noe CR (1995) Synthesis 1123
23. Kinetic and thermodynamic control in lactol acetalisations are incorrectly discussed in Nemoto H (1994) Tetrahedron Lett 35: 7785
24. exo-C*) was forced to -58° (cf. Ref. [4a]) during the calculations. 1296 conformations were sampled for each diasteromeric acetal. Calculations were performed on a Silicon Graphics Indigo 2/R4400
25. Robin MB, Bovey FA, Basch H in Zabicky J (ed) (1970) The Chemistry of Amides. Wiley, London, pp 1-72
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