The stereochemistry of addition of allyl sulfone carbanions to aldehydes.Formation of dihydrofurans

Arkivoc

Volumn 2002, Issue 8, 2002, Pages 157-165

  Hassner, Alfred ^a   Laxer, Avital ^a   Ghera, Eugene ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

Aldehydes; Allyl sulfones; Carbanaions; Dihydrofurans; Li chelation; Michael additions

Indexed keywords

1 BENZENESULFONYL 2 METHYLENE 3 HYDROXYPROPANE; 4 METHYL 2 PENTYL 3 BENZENESULFONYL 2,5 DIHYDROFURAN; 4 METHYL 3 BENZENESULFONYL 2 (4 NITROPHENYL) 2,5 DIHYDROFURAN; 4 METHYL 3 BENZENESULFONYL 2 (4 TOLYL) 2,5 DIHYDROFURAN; 4 METHYL 3 BENZENESULFONYL 2 PROPYL 2,5 DIHYDROFURAN; 4 METHYLENE 2 (4 NITROPHENYL) 3 BENZENESULFONYLTETRAHYDROFURAN; 4 NITROBENZALDEHYDE; ALDEHYDE DERIVATIVE; BROMOALLYLSULFONE; FURAN DERIVATIVE; HEMPA; LITHIUM ION; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHELATION; DRUG SYNTHESIS; HIGH TEMPERATURE; STEREOCHEMISTRY;

EID: 3242792443     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (11)

1. Stereochemistry 94. For Part 93 see Kumareswaran, R.; Hassner, A. Tetrahedron Asymmetry 2001, 12, 3409.
2. (a) Ghera, E.; Yehezkel, T.; Hassner, A. Tetrahedron Lett. 1990, 31, 3653.
3. (b) ibid. J. Org. Chem. 1996, 61, 4959.
4. (a) Ghera, E.; Yehezkel, T.; Hassner, A. J. Org. Chem. 1993, 58, 6716.
5. (b) Hassner, A.; Ghera, E.; Yechezkel, T.; Kleiman, V.; Balasubramanian, T.; Ostercamp, D. Pure Appl. Chem. 2000, 72, 1671.
6. (c) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755.
7. For a review see Boivin, T.L.B. Tetrahedron 1987, 43, 3309.
8. Najera, C.; Sansano, J.M. Tetrahedron Lett. 1992, 33, 6543.
9. 2 and the OH are part of the extended chain and the R- and allyl bromide substituents can be syn- or anti- oriented.
10. 2 and allyl bromide).
11. Ghera, E.; Yechezkel, T.; Hassner, A. J. Org. Chem. 1990, 55, 5977.