Domino reactions that combine an Azido-Schmidt ring expansion with the Diels-Alder reaction

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4993-4995

  Zeng, Yibin ^a   Reddy, D Srinivasa ^a   Hirt, Erin ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; HETEROCYCLIC COMPOUND; KETONE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; MOLECULE; X RAY CRYSTALLOGRAPHY;

AZIDES; HETEROCYCLIC COMPOUNDS, 2-RING; HETEROCYCLIC COMPOUNDS, 3-RING; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 12344322478     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047809r     Document Type: Article

References (19)

1. For reviews of domino processes, see: (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. (c) Waldmann, H. Organic Synthesis Highlights II; Wiley-VCH: Weinheim, 1995; pp 193-202. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (e) Padwa, A. Chem. Commun. 1998, 1417-1424. (f) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322.
2. For reviews of domino processes, see: (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. (c) Waldmann, H. Organic Synthesis Highlights II; Wiley-VCH: Weinheim, 1995; pp 193-202. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (e) Padwa, A. Chem. Commun. 1998, 1417-1424. (f) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322.
3. For reviews of domino processes, see: (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. (c) Waldmann, H. Organic Synthesis Highlights II; Wiley-VCH: Weinheim, 1995; pp 193-202. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (e) Padwa, A. Chem. Commun. 1998, 1417-1424. (f) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322.
4. For reviews of domino processes, see: (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. (c) Waldmann, H. Organic Synthesis Highlights II; Wiley-VCH: Weinheim, 1995; pp 193-202. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (e) Padwa, A. Chem. Commun. 1998, 1417-1424. (f) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322.
5. For reviews of domino processes, see: (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. (c) Waldmann, H. Organic Synthesis Highlights II; Wiley-VCH: Weinheim, 1995; pp 193-202. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (e) Padwa, A. Chem. Commun. 1998, 1417-1424. (f) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322.
6. For reviews of domino processes, see: (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. (c) Waldmann, H. Organic Synthesis Highlights II; Wiley-VCH: Weinheim, 1995; pp 193-202. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (e) Padwa, A. Chem. Commun. 1998, 1417-1424. (f) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322.
7. (a) Aubé, J.; Milligan, G. L.; Mossman, C. J. J. Org. Chem. 1992, 57, 1635-1637.
8. (b) Desai, P.; Schildknegt, K.; Agrios, K. A.; Mossman, C.; Milligan, G. L.; Aubé, J. J. Am. Chem. Soc. 2000, 122, 7226-7232.
9. (a) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965-8966.
10. (b) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449-10459.
11. Reddy, D. S.; Judd, W. R.; Aubé, J. Org. Lett. 2003, 5, 3899-3902.
12. A single example of an intramolecular variant of an analogous reaction to that shown in Scheme 1b was published in the context of a total synthesis of stenine: Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316-4318. To our knowledge, this is the only example of a tandem process involving any variation of the Schmidt reaction prior to the present work.
13. There are many examples of domino reactions involving the Diels-Alder reaction (see reviews listed in ref 1). Some recent examples include: (a) Akai, S.; Tanimoto, K.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 1407-1410. (b) Sabitha, G.; Reddy, E. V.; Fatima, N.; Yadav, J. S.; Krishna, K. V. S. R.; Kunwar, A. C. Synthesis 2004, 1150-1154. (c) Tietze, L. F.; Rackelmann, N.; Mueller, I. Chem. Eur. J. 2004, 10, 2722-2731. (d) Tietze, L. F.; Rackelmann, N. Z. Naturforsch. B: Chem. Sci. 2004, 59, 468-477. (e) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493-3497. (f) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260-12261.
14. There are many examples of domino reactions involving the Diels-Alder reaction (see reviews listed in ref 1). Some recent examples include: (a) Akai, S.; Tanimoto, K.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 1407-1410. (b) Sabitha, G.; Reddy, E. V.; Fatima, N.; Yadav, J. S.; Krishna, K. V. S. R.; Kunwar, A. C. Synthesis 2004, 1150-1154. (c) Tietze, L. F.; Rackelmann, N.; Mueller, I. Chem. Eur. J. 2004, 10, 2722-2731. (d) Tietze, L. F.; Rackelmann, N. Z. Naturforsch. B: Chem. Sci. 2004, 59, 468-477. (e) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493-3497. (f) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260-12261.
15. There are many examples of domino reactions involving the Diels-Alder reaction (see reviews listed in ref 1). Some recent examples include: (a) Akai, S.; Tanimoto, K.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 1407-1410. (b) Sabitha, G.; Reddy, E. V.; Fatima, N.; Yadav, J. S.; Krishna, K. V. S. R.; Kunwar, A. C. Synthesis 2004, 1150-1154. (c) Tietze, L. F.; Rackelmann, N.; Mueller, I. Chem. Eur. J. 2004, 10, 2722-2731. (d) Tietze, L. F.; Rackelmann, N. Z. Naturforsch. B: Chem. Sci. 2004, 59, 468-477. (e) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493-3497. (f) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260-12261.
16. There are many examples of domino reactions involving the Diels-Alder reaction (see reviews listed in ref 1). Some recent examples include: (a) Akai, S.; Tanimoto, K.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 1407-1410. (b) Sabitha, G.; Reddy, E. V.; Fatima, N.; Yadav, J. S.; Krishna, K. V. S. R.; Kunwar, A. C. Synthesis 2004, 1150-1154. (c) Tietze, L. F.; Rackelmann, N.; Mueller, I. Chem. Eur. J. 2004, 10, 2722-2731. (d) Tietze, L. F.; Rackelmann, N. Z. Naturforsch. B: Chem. Sci. 2004, 59, 468-477. (e) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493-3497. (f) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260-12261.
17. There are many examples of domino reactions involving the Diels-Alder reaction (see reviews listed in ref 1). Some recent examples include: (a) Akai, S.; Tanimoto, K.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 1407-1410. (b) Sabitha, G.; Reddy, E. V.; Fatima, N.; Yadav, J. S.; Krishna, K. V. S. R.; Kunwar, A. C. Synthesis 2004, 1150-1154. (c) Tietze, L. F.; Rackelmann, N.; Mueller, I. Chem. Eur. J. 2004, 10, 2722-2731. (d) Tietze, L. F.; Rackelmann, N. Z. Naturforsch. B: Chem. Sci. 2004, 59, 468-477. (e) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493-3497. (f) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260-12261.
18. There are many examples of domino reactions involving the Diels-Alder reaction (see reviews listed in ref 1). Some recent examples include: (a) Akai, S.; Tanimoto, K.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 1407-1410. (b) Sabitha, G.; Reddy, E. V.; Fatima, N.; Yadav, J. S.; Krishna, K. V. S. R.; Kunwar, A. C. Synthesis 2004, 1150-1154. (c) Tietze, L. F.; Rackelmann, N.; Mueller, I. Chem. Eur. J. 2004, 10, 2722-2731. (d) Tietze, L. F.; Rackelmann, N. Z. Naturforsch. B: Chem. Sci. 2004, 59, 468-477. (e) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493-3497. (f) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260-12261.
19. All azides and other starting materials were prepared using standard methods; see Supporting Information for details. All azides should be used with caution!