Improved Cr(II)-mediated synthesis of E-alkenylstannanes from aldehydes using Bu3SnCHI2 in DMF

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6419-6420

  Hodgson, David M ^a   Foley, Anne M ^a   Lovell, Peter J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alkenes; Alkenylation; Chromium and compounds; Tin and compounds

Indexed keywords

ALDEHYDE; CHROMIUM; TIN;

ARTICLE; COLUMN CHROMATOGRAPHY; SYNTHESIS;

EID: 0032572904     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01325-2     Document Type: Article

References (14)

1. [1] Davies AG. Organotin chemistry. Weinheim: VCH, 1997; Mitchell TN. Organotin reagents in cross-coupling. In: Diederich F, Stang PJ, editors. Metal-catalyzed cross-coupling reactions. Chichester: Wiley-VCH, 1997:167-202; Farina V, Krishnamurthy V, Scott WJ. Org. React. 1997;50:1-652.
2. [1] Davies AG. Organotin chemistry. Weinheim: VCH, 1997; Mitchell TN. Organotin reagents in cross-coupling. In: Diederich F, Stang PJ, editors. Metal-catalyzed cross-coupling reactions. Chichester: Wiley-VCH, 1997:167-202; Farina V, Krishnamurthy V, Scott WJ. Org. React. 1997;50:1-652.
3. [1] Davies AG. Organotin chemistry. Weinheim: VCH, 1997; Mitchell TN. Organotin reagents in cross-coupling. In: Diederich F, Stang PJ, editors. Metal-catalyzed cross-coupling reactions. Chichester: Wiley-VCH, 1997:167-202; Farina V, Krishnamurthy V, Scott WJ. Org. React. 1997;50:1-652.
4. [2] (a) Hodgson DM, Boulton LT, Maw GN. Tetrahedron 1995;51:3713-3724;
5. (b) Recent reviews: Hodgson DM, Boulton LT. Chromium-and titanium-mediated synthesis of alkenes from carbonyl compounds. In: Williams JMJ, editor. Preparation of alkenes: a practical approach. Oxford: OUP, 1996:81-93; Hodgson DM, Comina PJ. Chromium-mediated C-C coupling reactions. In: Beller M, Bolm C, editors. Transition metals for organic synthesis. Chichester: Wiley-VCH, 1998:418-424.
6. (b) Recent reviews: Hodgson DM, Boulton LT. Chromium-and titanium-mediated synthesis of alkenes from carbonyl compounds. In: Williams JMJ, editor. Preparation of alkenes: a practical approach. Oxford: OUP, 1996:81-93; Hodgson DM, Comina PJ. Chromium-mediated C-C coupling reactions. In: Beller M, Bolm C, editors. Transition metals for organic synthesis. Chichester: Wiley-VCH, 1998:418-424.
7. [3] Hodgson DM, Boulton LT, Maw GN. Synlett 1995:267-268; Boyce RJ, Pattenden G. Tetrahedron Lett. 1996;37:3501-3504; Smith III AB, Ott GR. J. Am. Chem. Soc. 1998;120:3935-3948.
8. [3] Hodgson DM, Boulton LT, Maw GN. Synlett 1995:267-268; Boyce RJ, Pattenden G. Tetrahedron Lett. 1996;37:3501-3504; Smith III AB, Ott GR. J. Am. Chem. Soc. 1998;120:3935-3948.
9. [3] Hodgson DM, Boulton LT, Maw GN. Synlett 1995:267-268; Boyce RJ, Pattenden G. Tetrahedron Lett. 1996;37:3501-3504; Smith III AB, Ott GR. J. Am. Chem. Soc. 1998;120:3935-3948.
10. [4] Chong JM, Park SB. J. Org. Chem. 1993;58:523-527.
11. 2 (ref. 2a) [NaI, acetone, 25 °C, 24 h (quant.)] and used without further purification.
12. 2 in DMF gives recovered ketone (quant.), see also ref. 7).
13. [7] Okazoe T, Takai K, Utimoto K. J. Am. Chem. Soc. 1987;109:951-953.
14. [8] Takai K, Kataoka Y, Okazoe T, Utimoto K. Tetrahedron Lett. 1987;28:1443-1446.