ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Selective Preparation of l- or u-Aldols from Ethyl Trityl Ketone and Aromatic Aldehydes through Lithium and Aluminium Enolates, RespectivelyThe ethyl trityl ketone (1) is deprotonated to the (Z)-enolate 2 which adds to aromatic aldehydes with relative topicity ul to give the aldols 3(-78°, THF, kinetic control). If, on the other hand, 1 is heated with trimethylaluminium in toluene, the aluminium enolate formed combines with aromatic aldehydes and with cinnamic aldehyde with opposite relative topicity (lk) to the aldols 5 (+20°, toluene, 2 d, precipitation of the aluminium aldolate 4, thermodynamic control). The mechanism is discussed (cf. Fig. 1). The adducts to benzaldehyde (3a, 5a), furfural (3f, 5f), and cinnamaldehyde (3i, 5i) are O-(2-methoxyethoxy)methyl (MEM) protected and cleaved by lithium triethylborohydride to the 1,3-diol derivatives 9-11 with a free primary and a protected secondary OH-group. Analogous conversions of 1 and other ketones may also be diastereoselective, but turned out to be of less preparative value (see 6-8, 12).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680421
