Remote allylic silyloxy groups as stereocontrol elements in intramolecular oxymercurations of γ-hydroxyalkenes

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 2109-2117

  Bratt, Katharina ^a,b   Garavelas, Agatha ^a   Perlmutter, Patrick ^a   Westman, Gunnar ^a  

^a MONASH UNIVERSITY   (Australia)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENOLS; DIASTEREO-SELECTIVITY; DIASTEREOMERS; DIASTEREOSELECTION; ENANTIOSELECTIVE SYNTHESIS; PROTECTING GROUP; STEREOCONTROL;

ACETONITRILE; DICHLOROMETHANE; OLEFINS; OXYGEN;

CYCLIZATION;

EID: 0000358288     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951853q     Document Type: Article

References (24)

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7. The stereochemistry for the "c" series is enantiomeric to that shown in Scheme 1 but has been left as shown for simplicity.
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18. We have also briefly examined the use of Evans' valine-derived auxiliary in this chemistry. We were rewarded with a crystalline material for the major diastereomer ii of the ring closure (see below). This clearly confirmed the syn relative stereochemistry between C6 and C8 (Garavelas, A. Ph.D. Thesis, Monash University, 1995). (Chemical Equation Presented).
19. Kitching, W.; Drew, G. M.; Alberts, V. Organometallics 1982, 1, 331.
20. A related approach employing intramolecular oxymercurations of allenes has been reported. See: (a) Walkup, R. D.; Kim, S. W. J. Org. Chem. 1994, 59, 3433.
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24. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.