ISSN:
0947-3440
Keywords:
Asymmetric synthesis
;
Primary amines
;
Nucleophilic 1,2-addition
;
N—N bond cleavage
;
Hydrazones
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The aldehydes 1 or 5 are converted to the SAMP hydrazones 2 or the α-alkylated SAMP hydrazones 7 and treated with organolithium compounds at low temperature. Cleavage of the N—N bond of the resulting hydrazines 3 and 8 with Raney-Ni/H2, or of the N-methoxycarbonylhydrazines 9 with Li/NH3, yield the amines 4 with 61-90% ee, the amines 11 with 45-96% de and 93 → 99% ee. The absolute configuration of the amines 11 was established by X-ray analysis of an appropriate MTPA derivative.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970608
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