Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1387-1390

  Zhu, Xue Feng ^a   Henry, Christopher E ^a   Wang, Jay ^a   Dudding, Travis ^a,b   Kwon, Ohyun ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; DIOXANE DERIVATIVE; ESTER DERIVATIVE; PHOSPHINE; PHOSPHONIUM DERIVATIVE;

ARTICLE; CATALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 17444432653     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050203y     Document Type: Article

References (38)

1. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
2. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
3. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
4. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
5. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
6. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
7. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
8. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
9. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
10. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
11. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
12. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
13. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (d) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682. (e) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (f) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129. (g) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901. (h) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677. (i) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (j) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. T.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227. (k) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (l) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (m) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
14. Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
15. Reaction of ethyl 2,3-butadienoate with aldehydes in the presence of DABCO gave the normal Baylis - Hillman adducts. See: Tsuboi, S.; Kuroda, H.; Takatsuka, S.; Fukawa, T.; Sakai, T.; Utaka, M. J. Org. Chem. 1993, 58, 5952.
16. Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461.
17. The connectivity and relative stereochemistry of these compounds were confirmed by X-ray crystallographic analysis. Crystallographic data for 3-E and 3-Z have been deposited with the Cambridge Crystallographic Data Centre as supplementary numbers CCDC 250757 and 250758. CCDC 250757 and 250758 contain the supplementary crystallographic data for this paper. These data can be obtained online free of charge (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB2 IEZ, U.K..; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
18. For detailed information, see Supporting Information.
19. For the preparation of alkyl allenoates 1, see Supporting Information.
20. For examples, see: (a) Perlmutter, P.; Puniani, E.; Westman, G. Tetrahedron Lett. 1996, 37, 1715. (b) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (c) Lee, W.; Yang, K.; Chen, K. Chem. Commun. 2001, 1612.
21. For examples, see: (a) Perlmutter, P.; Puniani, E.; Westman, G. Tetrahedron Lett. 1996, 37, 1715. (b) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (c) Lee, W.; Yang, K.; Chen, K. Chem. Commun. 2001, 1612.
22. For examples, see: (a) Perlmutter, P.; Puniani, E.; Westman, G. Tetrahedron Lett. 1996, 37, 1715. (b) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (c) Lee, W.; Yang, K.; Chen, K. Chem. Commun. 2001, 1612.
23. For the synthesis of dihydrofuran 5, see: (a) Kolsaker, P.; Jørgensen, T.; Wøien Larsen, G. Tetrahedron 1974, 30, 3393. (b) Hudlicky, T.; Fleming, A.; Lovelace, T. C. Tetrahedron 1989, 45, 3021.
24. For the synthesis of dihydrofuran 5, see: (a) Kolsaker, P.; Jørgensen, T.; Wøien Larsen, G. Tetrahedron 1974, 30, 3393. (b) Hudlicky, T.; Fleming, A.; Lovelace, T. C. Tetrahedron 1989, 45, 3021.
25. (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
26. (b) Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736.
27. Evans, D. A.; Gauchet-Prunet, J. A. J. Org. Chem. 1993, 58, 2446.
28. For examples, see: (a) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Khan, A. A. Chem. Ber. 1990, 123, 1447. (b) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317. (c) Reference 8.
29. For examples, see: (a) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Khan, A. A. Chem. Ber. 1990, 123, 1447. (b) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317. (c) Reference 8.
30. For examples, see: (a) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Khan, A. A. Chem. Ber. 1990, 123, 1447. (b) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317. (c) Reference 8.
31. Zhao, G.; Huang, J.; Shi, M. Org. Lett. 2003, 5, 4737.
32. Evans, C. A.; Miller, S. J. J. Am. Chem. Soc. 2003, 125, 12394.
33. A substituent at α-carbon of allenoates can deflect the inherent reactivity pattern of nonsubstituted allenoates. For an example, see ref 2.
34. It is noteworthy that both the E- and Z-isomer provide one δ-hydroxy-β-ketoester.
35. (a) Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
36. (b) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 1.1.
37. Macrolide Antibiotics. Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: Orlando, FL, 1984.
38. Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836.