Collect. Czech. Chem. Commun. 2003, 68, 885-898
https://doi.org/10.1135/cccc20030885

Diastereoselective Addition of α-Metalated Sulfoxides to Imines Revisited: Mechanism, Computational Studies, and the Effect of External Chiral Ligands

Brian Pedersen, Tobias Rein, Inger Søtofte, Per-Ola Norrby* and David Tanner*

Department of Chemistry, Technical University of Denmark, Buildings 201 and 207, Kemitorvet, DK-2800 Kgs. Lyngby, Denmark

References

1a. Solladié G.: Pure Appl. Chem. 1988, 60, 1699. <https://doi.org/10.1351/pac198860111699>
1b. Walker A. J.: Tetrahedron: Asymmetry 1992, 3, 961. <https://doi.org/10.1016/S0957-4166(00)86026-7>
2a. Bravo P., Capelli S., Crucianelli M., Guidetti M., Markovsky A. L., Meille S. V., Soloshonok V. A., Sorochinsky A. E., Viani F., Zanda M.: Tetrahedron 1999, 55, 3025. <https://doi.org/10.1016/S0040-4020(99)00064-2>
2b. Volonterio A., Bravo P., Pesenti C., Zanda M.: Tetrahedron Lett. 2001, 42, 3985. <https://doi.org/10.1016/S0040-4039(01)00651-7>
3a. Bloch R.: Chem. Rev. (Washington, D. C.) 1998, 98, 1407. <https://doi.org/10.1021/cr940474e>
3b. Pettinari C., Pellei M., Cavicchio G., Crucianelli M., Panzeri W., Colapietro M., Cassetta A.: Organometallics 1999, 18, 555. <https://doi.org/10.1021/om9808460>
3c. Naimi-Jamal M. R., Ipaktschi J., Saidi M. R.: Eur. J. Org. Chem. 2000, 1735. <https://doi.org/10.1002/(SICI)1099-0690(200005)2000:9<1735::AID-EJOC1735>3.0.CO;2-A>
3d. Sivakumar A. V., Babu G. S., Bhat S. V.: Tetrahedron: Asymmetry 2001, 12, 1095. <https://doi.org/10.1016/S0957-4166(01)00185-9>
3e. Zucca C., Bravo P., Corradi E., Meille S. V., Volonterio A., Zanda M.: Molecules 2001, 6, 424. <https://doi.org/10.3390/60500424>
3f. Cabiddu S., Cadoni E., Ianni A., Gelli G., Melis S., Bernard A. M., Cabiddu M. G., De Montis S., Fattuoni C.: Eur. J. Org. Chem. 2002, 3393. <https://doi.org/10.1002/1099-0690(200210)2002:20<3393::AID-EJOC3393>3.0.CO;2-4>
4. Tsuchihashi G.-I., Iriuchijima S., Maniwa K.: Tetrahedron Lett. 1973, 3389. <https://doi.org/10.1016/S0040-4039(01)86922-7>
5. Ronan B., Marchalin S., Samuel O., Kagan H. B.: Tetrahedron Lett. 1988, 29, 6101. <https://doi.org/10.1016/S0040-4039(00)82275-3>
6a. Pyne S. G., Dikic B.: J. Chem. Soc., Chem. Commum. 1989, 826. <https://doi.org/10.1039/c39890000826>
6b. Pyne S. G., Boche G.: J. Org. Chem. 1989, 54, 2663. <https://doi.org/10.1021/jo00272a040>
7. Pedersen B.: Ph.D. Thesis. Technical University of Denmark, Lyngby 2001.
8. See, for example: Hubbard J. S., Harris T. M.: J. Org. Chem. 1981, 46, 2566. We are indebted to Prof. G. Solladié (Strasbourg) for pointing out the advantages of using demetalated silica gel. <https://doi.org/10.1021/jo00325a026>
9. http://www.schrodinger.com.
10a. Gillies M. B., Tønder J. E., Tanner D., Norrby P.-O.: J. Org. Chem. 2002, 67, 7378. <https://doi.org/10.1021/jo0262107>
10b. Mader M. M., Norrby P.-O.: Chem. Eur. J. 2002, 8, 5043. <https://doi.org/10.1002/1521-3765(20021104)8:21<5043::AID-CHEM5043>3.0.CO;2-R>
11. For the use of an external chiral ligand to enhance the diastereoselectivity of addition of an α-lithiated sulfoxide to a nitrone, see: Murahashi S.-I., Sun J., Tsuda T.: Tetrahedron Lett. 1993, 34, 2645. <https://doi.org/10.1016/S0040-4039(00)77646-5>
12a. For 1a: Balachandran K. S., Bhatnagar I., George M. V.: J. Org. Chem. 1968, 33, 3891. <https://doi.org/10.1021/jo01274a043>
12b. for 1b: Okubo M., Ueda S.: Bull. Chem. Soc. Jpn. 1979, 52, 3346.
12c. for 1c and 1d: Roe A., Montgomery J. A.: J. Am. Chem. Soc. 1953, 75, 910. <https://doi.org/10.1021/ja01100a040>
12d. for 1e: Grigg R., Mitchell T. R. B., Tongpenyai N.: Synthesis 1981, 442. <https://doi.org/10.1055/s-1981-29474>
12e. for 1f: Jennings W. B., Lovely C. J.: Tetrahedron Lett. 1988, 29, 3725. <https://doi.org/10.1016/S0040-4039(00)82164-4>
13. Flack H. D.: Acta Crystallogr., Sect. A: Fundam. Crystallogr. 1983, 39, 876. <https://doi.org/10.1107/S0108767383001762>
14. Siemens: SMART and SAINT, Area-Detector Control and Integration Software. Bruker AXS Analytical X-Ray Systems, Madison (WI) 1995.
15. Sheldrick G. M.: SADABS, Program for Absorption Correction. Bruker AXS Analytical X-Ray Systems, Madison (WI) 1996.
16. Sheldrick G. M.: SHELXTL version 5.03. Bruker AXS Analytical X-Ray Systems, Madison (WI) 1994.
17. Spek A. L.: Acta Crystallogr., Sect. A: Fundam. Crystallogr. 1990, 46, C-34.