Aldol condensation reactions of (dienone) tricarbonyliron complexes. 41. Enantioselective total synthesis of 3-deoxypentoses from (−)-myrtenal

Autor:	Michel Franck-Neumann, Philippe Geoffroy, Paul Bissinger
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Trimethylsilyl Chemistry Stereochemistry Organic Chemistry Diastereomer Enantioselective synthesis Total synthesis Biochemistry chemistry.chemical_compound Aldol reaction Drug Discovery Enol ether Aldol condensation Lewis acids and bases
Zdroj:	Tetrahedron Letters. 38:4477-4478
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(97)00906-4
Popis:	The trimethylsilyl enol ether of the tricarbonyliron complex (−)- 1 deriving from (R)-(−)-myrtenal undergoes higly stereoselective cross aldol reactions with TiCl 4 -coordinated β-alkoxyaldehydes. With BF 3 ,Et 2 O as Lewis acid the reaction is only poorly stereoselective, allowing the synthesis of pairs of easily separable diastereomeric optically active ketols. These features are useful to have access to chiral polyols, as illustrated here by the synthesis of the protected deoxypentoses (+)- 10 and (−)- 11 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::35367905545764338dff5977d973fc01 https://doi.org/10.1016/s0040-4039(97)00906-4 Zobrazit plný text záznamu Full Text from ScienceDirect