Tandem silylformylation-allyl(crotyl)silylation: A new approach to polyketide synthesis

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 8889-8900

  Zacuto, Michael J ^a   O'Malley, Steven J ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Allylation; Carbonylation; Polyketides; Silylformylation; Strain release Lewis acidity

Indexed keywords

ALDEHYDE; ALKENE; ALKYNE; CARBON; LEWIS ACID; OXASILACYCLOPENTANE; PENTANE; POLYKETIDE; SILICON; UNCLASSIFIED DRUG;

ACIDITY; ALLYLSILYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; METHODOLOGY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SILYLATION; SILYLFORMYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0142217511     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.04.004     Document Type: Article

References (70)

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16. 3, followed by 2 equiv. of allylMgBr. This reaction provides the desired diallylsilyl ethers in 50-90% yields, with more sterically hindered alcohols giving better results.
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19. This procedure was adapted from the reported method for the synthesis of (Z)-crotyltrichlorosilane: (a) Tsuji J., Hara M., Ohno K. Tetrahedron. 30:1974;2143-2146 (b) Kira M., Hino T., Sakurai H. Tetrahedron Lett. 30:1989;1099-1102 (c) Iseki K., Kuroki Y., Takahashi M., Kishimoto S., Kobayashi Y. Tetrahedron. 53:1997;3513-3526.
20. This procedure was adapted from the reported method for the synthesis of (Z)-crotyltrichlorosilane: (a) Tsuji J., Hara M., Ohno K. Tetrahedron. 30:1974;2143-2146 (b) Kira M., Hino T., Sakurai H. Tetrahedron Lett. 30:1989;1099-1102 (c) Iseki K., Kuroki Y., Takahashi M., Kishimoto S., Kobayashi Y. Tetrahedron. 53:1997;3513-3526.
21. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
22. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
23. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
24. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
25. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
26. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
27. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
28. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
29. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
30. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
31. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
32. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
33. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
34. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
35. The silane alcoholysis literature prior to 1985 has been reviewed. See: (a) Lukevics E., Dzintara M. J. Organomet. Chem. 295:1985;265-315. See also: (b) Caseri W., Pregosin P.S. Organometallics. 7:1988;1373-1380 (c) Yamamoto K., Takemae M. Bull. Chem. Soc. Jpn. 62:1989;2111-2113 (d) Luo X.-L., Crabtree R.H. J. Am. Chem. Soc. 111:1989;2527-2535 (e) Doyle M.P., High K.G., Bagheri V., Pieters R.J., Lewis P.J., Pearson M.M. J. Org. Chem. 55:1990;6082-6086 (f) Bedard T.C., Corey J.Y. J. Organomet. Chem. 428:1992;315-333 (g) Barton D.H.R., Kelly M.J. Tetrahedron Lett. 33:1992;5041-5044 (h) Burn M.J., Bergman R.G. J. Organomet. Chem. 472:1994;43-54 (i) Gregg B.T., Cutler A.R. Organometallics. 13:1994;1039-1043 (j) Lorenz C., Schubert U. Chem. Ber. 128:1995;1267-1269 (k) Chang S., Scharrer E., Brookhart M. J. Mol. Catal. A. 130:1998;107-119 (l) Ito H., Ishizuka T., Okumura T., Yamanaka H., Tateiwa J.-I., Sonada M., Hosomi A. J. Organomet. Chem. 574:1999;102-106 (m) Blackwell J.M., Foster K.L., Beck V.H., Piers W.E. J. Org. Chem. 64:1999;4887-4892 (n) Le Bideau F., Coradin T., Hénique J., Samuel E. Chem. Commun. 2001;1408-1409 (o) Chung M.K., Ferguson G., Robertson V. Can. J. Chem. 79:2001;949-957.
36. For a seminal report on the monoalcoholysis of a dihydrosilane, see: Corriu R.J.P., Moreau J.J.E. J. Organomet. Chem. 120:1976;337-346.
37. Indeed, tandem alcoholysis-hydrosilylation using dihydrosilanes and allylic and homoallylic alcohols has been described. See: (a) Corriu R.J.P., Moreau J.J.E. J. Organomet. Chem. 114:1976;135-144 (b) Xin S., Harrod J.F. J. Organomet. Chem. 499:1995;181-191 (c) Wang X., Ellis W.W., Bosnich B. Chem. Commun. 1996;2561-2562.
38. Indeed, tandem alcoholysis-hydrosilylation using dihydrosilanes and allylic and homoallylic alcohols has been described. See: (a) Corriu R.J.P., Moreau J.J.E. J. Organomet. Chem. 114:1976;135-144 (b) Xin S., Harrod J.F. J. Organomet. Chem. 499:1995;181-191 (c) Wang X., Ellis W.W., Bosnich B. Chem. Commun. 1996;2561-2562.
39. Indeed, tandem alcoholysis-hydrosilylation using dihydrosilanes and allylic and homoallylic alcohols has been described. See: (a) Corriu R.J.P., Moreau J.J.E. J. Organomet. Chem. 114:1976;135-144 (b) Xin S., Harrod J.F. J. Organomet. Chem. 499:1995;181-191 (c) Wang X., Ellis W.W., Bosnich B. Chem. Commun. 1996;2561-2562.
40. All chiral alcohol starting materials used in this study were racemic.
41. The diacetate was prepared to facilitate analysis of the diastereoselectivity by gas chromatography. The diol may be isolated.
42. (a) Furuya N., Sukawa T. J. Organomet. Chem. 96:1975;C1-C3
43. (b) Kira M., Hino T., Sakurai H. Tetrahedron Lett. 30:1989;1099-1102
44. (c) Iseki K., Kuroki Y., Takahashi M., Kishimoto S., Kobayashi Y. Tetrahedron. 53:1997;3513-3526.
45. Reetz M.T., Jung A., Bolm C. Tetrahedron. 44:1988;3889-3898.
46. Uyeo S., Itani H. Tetrahedron Lett. 32:1991;2143-2146.
47. Linderman R.J., Chen K. J. Org. Chem. 61:1996;2441-2453.
48. Matsumoto K., Oshima K., Utimoto K. J. Org. Chem. 59:1994;7152-7155.
49. (a) Myers A.G., Kephart S.E., Chen H. J. Am. Chem. Soc. 114:1992;7922-7923. For another example of an uncatalyzed silicon-mediated aldol reaction, see: (b) Myers A.G., Widdowson K.L. J. Am. Chem. Soc. 112:1990;9672-9674 (c) Myers A.G., Widdowson K.L., Kukkola P. J. Am. Chem. Soc. 114:1992;2765-2767.
50. (a) Myers A.G., Kephart S.E., Chen H. J. Am. Chem. Soc. 114:1992;7922-7923. For another example of an uncatalyzed silicon-mediated aldol reaction, see: (b) Myers A.G., Widdowson K.L. J. Am. Chem. Soc. 112:1990;9672-9674 (c) Myers A.G., Widdowson K.L., Kukkola P. J. Am. Chem. Soc. 114:1992;2765-2767.
51. (a) Myers A.G., Kephart S.E., Chen H. J. Am. Chem. Soc. 114:1992;7922-7923. For another example of an uncatalyzed silicon-mediated aldol reaction, see: (b) Myers A.G., Widdowson K.L. J. Am. Chem. Soc. 112:1990;9672-9674 (c) Myers A.G., Widdowson K.L., Kukkola P. J. Am. Chem. Soc. 114:1992;2765-2767.
52. (a) Denmark S.E., Griedel B.D., Coe D.M. J. Org. Chem. 58:1993;988-990
53. (b) Denmark S.E., Griedel B.D., Coe D.M., Schnute M.E. J. Am. Chem. Soc. 116:1994;7026-7043.
54. Denmark S.E., Jacobs R.T., Dai-Ho G., Wilson S. Organometallics. 9:1990;3015-3019.
55. Several relevant X-ray structures have been reported. See, for example: Shaw J.T., Woerpel K.A. J. Org. Chem. 62:1997;6706-6707.
56. Hoveyda has reported relevant observations regarding the Lewis acidity of oxasilacyclopentanes of this type. See: Young D.G.J., Hale M.R., Hoveyda A.H. Tetrahedron Lett. 37:1996;827-830.
57. These are the conditions employed by Utimoto. See Ref. 18.
58. Myers has elegantly established a mechanism involving pseudorotation for the uncatalyzed aldol reactions of O-silyl ketene N,O-acetals. See Ref. 19c.
59. (a) Stevenson W.H. III., Wilson S., Martin J.C., Farnham W.B. J. Am. Chem. Soc. 107:1985;6340-6352
60. (b) Stevenson W.H. III, Martin J.C. J. Am. Chem. Soc. 107:1985;6352-6358.
61. Schmidt D.R., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 125:2003;1190-1191.
62. Kira and Sakurai, and Roush and Chemler have made similar observations during studies of intramolecular crotylsilylations of β-hydroxy ketones and aldehydes. See: (a) Sato K., Kira M., Sakurai H. J. Am. Chem. Soc. 111:1989;6429-6431 (b) Kira M., Sato K., Kazushi S., Gewald R., Sakurai H. Chem. Lett. 1995;281-282 (c) Chemler S.R., Roush W.R. J. Org. Chem. 63: 1998;3800-3801 (d) Chemler S.R., Roush W.R. Tetrahedron Lett. 40:1999;4643-4647 (e) Chemler S.R., Roush W.R. J. Org. Chem. 68:2003;1319-1333.
63. Kira and Sakurai, and Roush and Chemler have made similar observations during studies of intramolecular crotylsilylations of β-hydroxy ketones and aldehydes. See: (a) Sato K., Kira M., Sakurai H. J. Am. Chem. Soc. 111:1989;6429-6431 (b) Kira M., Sato K., Kazushi S., Gewald R., Sakurai H. Chem. Lett. 1995;281-282 (c) Chemler S.R., Roush W.R. J. Org. Chem. 63: 1998;3800-3801 (d) Chemler S.R., Roush W.R. Tetrahedron Lett. 40:1999;4643-4647 (e) Chemler S.R., Roush W.R. J. Org. Chem. 68:2003;1319-1333.
64. Kira and Sakurai, and Roush and Chemler have made similar observations during studies of intramolecular crotylsilylations of β-hydroxy ketones and aldehydes. See: (a) Sato K., Kira M., Sakurai H. J. Am. Chem. Soc. 111:1989;6429-6431 (b) Kira M., Sato K., Kazushi S., Gewald R., Sakurai H. Chem. Lett. 1995;281-282 (c) Chemler S.R., Roush W.R. J. Org. Chem. 63: 1998;3800-3801 (d) Chemler S.R., Roush W.R. Tetrahedron Lett. 40:1999;4643-4647 (e) Chemler S.R., Roush W.R. J. Org. Chem. 68:2003;1319-1333.
65. Kira and Sakurai, and Roush and Chemler have made similar observations during studies of intramolecular crotylsilylations of β-hydroxy ketones and aldehydes. See: (a) Sato K., Kira M., Sakurai H. J. Am. Chem. Soc. 111:1989;6429-6431 (b) Kira M., Sato K., Kazushi S., Gewald R., Sakurai H. Chem. Lett. 1995;281-282 (c) Chemler S.R., Roush W.R. J. Org. Chem. 63: 1998;3800-3801 (d) Chemler S.R., Roush W.R. Tetrahedron Lett. 40:1999;4643-4647 (e) Chemler S.R., Roush W.R. J. Org. Chem. 68:2003;1319-1333.
66. Kira and Sakurai, and Roush and Chemler have made similar observations during studies of intramolecular crotylsilylations of β-hydroxy ketones and aldehydes. See: (a) Sato K., Kira M., Sakurai H. J. Am. Chem. Soc. 111:1989;6429-6431 (b) Kira M., Sato K., Kazushi S., Gewald R., Sakurai H. Chem. Lett. 1995;281-282 (c) Chemler S.R., Roush W.R. J. Org. Chem. 63: 1998;3800-3801 (d) Chemler S.R., Roush W.R. Tetrahedron Lett. 40:1999;4643-4647 (e) Chemler S.R., Roush W.R. J. Org. Chem. 68:2003;1319-1333.
67. Dreher S.D., Leighton J.L. J. Am. Chem. Soc. 123:2001;341-342.
68. (a) Kinnaird J.W.A., Ng P.Y., Kubota K., Wang X., Leighton J.L. J. Am. Chem. Soc. 124:2002;7920-7921
69. (b) Wang X., Meng Q., Nation A.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;10672-10673
70. (c) Kubota K., Leighton J.L. Angew. Chem. Int. Ed. 42:2003;946-948.