Page 228 - Advanced Organic Chemistry Part B - Reactions & Synthesis

200 General References

CHAPTER 2
Aldol Additions and Condensations
Reactions of Carbon
Nucleophiles with
Carbonyl Compounds M. Braun in Advances in Carbanion Chemistry, Vol. 1. V. Snieckus, ed., JAI Press, Greenwich, CT, 1992.
D. A. Evans, J. V. Nelson, and T. R. Taber, Top. Stereochem., 13, 1 (1982).
A. S. Franklin and I. Paterson, Contemp. Org. Synth., 1, 317 (1994).
C. H. Heathcock, in Comprehensive Carbanion Chemistry, E. Buncel and T. Durst, ed., Elsevier,
Amsterdam, 1984.
C. H. Heathcock, in Asymmetric Synthesis, Vol. 3, J. D. Morrison, ed., Academic Press, New York, 1984.
R. Mahrwald, ed. Modern Aldol Reactions, Wiley-VCH, 2004.
S. Masamune, W. Choy, J. S. Petersen, and L. R. Sita, Angew. Chem. Int. Ed. Engl., 24, 1 (1985).
T. Mukaiyama, Org. React., 28, 203 (1982).
A. T. Nielsen and W. T. Houlihan, Org. React., 16, 1 (1968).
Annulation Reactions

R. E. Gawley, Synthesis, 777 (1976).
M. E. Jung, Tetrahedron, 32, 3 (1976).
Mannich Reactions

F. F. Blicke, Org. React., 1, 303 (1942).
H. Bohme and M. Heake, in Iminium Salts in Organic Chemistry, H. Bohmne and H. G. Viehe, ed.,
Wiley-Interscience, New York, 1976, pp. 107–223.
M. Tramontini and L. Angiolini, Mannich Bases: Chemistry and Uses, CRC Press, Boca Raton, FL, 1994.
Phosphorus-Stabilized Ylides and Carbanions
I. Gosney and A. G. Rowley in Organophosphorus Reagents in Organic Synthesis, J. I. G. Cadogan, ed.,
Academic Press, London, 1979, pp. 17–153.
A. W. Johnson, Ylides and Imines of Phosphorus, John Wiley, New York, 1993.
A. Maercker, Org. React., 14, 270 (1965).
W. S. Wadsworth, Jr., Org. React., 25, 73 (1977).

Conjugate Addition Reactions
P. Perlmatter, Conjugate Addition Reactions in Organic Synthesis, Permagon Press, New York, 1992.

Problems

(References for these problems will be found on page 1272.)
2.1 Predict the product formed in each of the following reactions:

1) NaOCH CH 3
2
(a) γ -butyrolactone + ethyl oxalate C H O 5
8 10
2) H +
ethanol
(b) 4-bromobenzaldehyde + ethyl cyanoacetate C H BrNO 2
12 10
piperidine
O
1) LiN(i-Pr) , –78°C
2
(c) CH CH CH CCH H O
2
2
3
3
2) CH CH CHO, 15 min C 8 16 2
3
2
3)H O
2
(d) O
NaOH, H O
2
O CHO + PhCH CCH 3 C 13 10 2
H O
2