Highly stereoselective chelation-controlled allylation and deuteration of α-chiral α,α'-dialkoxy radicals

Chemistry Letters

Volumn , Issue 10, 1996, Pages 845-846

  Nagano, Hajime ^a   Azuma, Yukiko ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005544634     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.845     Document Type: Article

References (21)

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2. N. A. Porter, B. Giese, and D. P. Curran, Acc. Chem. Res., 24, 296 (1991) ; W. Smadja, Synlett, 1994, 1; D. P. Curran, N. A. Porter, and B. Giese, "Stereochemistry of Radical Reactions; Concepts, Guidelines, and Synthetic Applications," VCH, Weinheim (1996).
3. N. A. Porter, B. Giese, and D. P. Curran, Acc. Chem. Res., 24, 296 (1991) ; W. Smadja, Synlett, 1994, 1; D. P. Curran, N. A. Porter, and B. Giese, "Stereochemistry of Radical Reactions; Concepts, Guidelines, and Synthetic Applications," VCH, Weinheim (1996).
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15. 2a
16. 2O/THF; viii, p-TsOH, acetone.
17. 2b. 2k
18. 2 (2.5 eq.) at room temperature gave 2a with lower diastereoselectivity.
19. 1H NMR spectra with those of 2a and 3a.
20. 2b, 2k
21. 1H NMR (400 MHz) integration of CHD. 4a: δ1.92 (m), 5a: δ 1.81 (ddt, J = 7.4, 5.6, and 2.0 Hz); 4b:δ1.86 (m); 5b δ 1.79 (m).