New Atropisomeric Amino Alcohol Ligands for Enantioselective Addition of Diethylzinc to Aldehydes

Efficient synthesis of several new atropisomeric amino alcohols having 1‐phenyl‐1H‐pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single‐crystal X‐ray measurement. The consequences of the size of the N‐substituents on enantioinduction were examined by employin...

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Bibliographic Details
Published in:	Chirality (New York, N.Y.) Vol. 27; no. 3; pp. 216 - 222
Main Authors:	Faigl, F., Deák, SZ, Erdélyi, ZS, Holczbauer, T., Czugler, M., Nyerges, M., Mátravölgyi, B.
Format:	Journal Article
Language:	English
Published:	United States Blackwell Publishing Ltd 01-03-2015 Wiley Subscription Services, Inc
Subjects:	Alcohols Aldehydes - chemistry amino alcohol Amino Alcohols - chemical synthesis aromatic aldehyde asymmetric catalysis axial chirality Catalysis Chirality Ligands Organometallic Compounds - chemistry selective hydrolysis Single crystals Special effects Stereoisomerism Synthesis X-rays aromatic aldehyde axial chirality amino alcohol asymmetric catalysis selective hydrolysis
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Summary:	Efficient synthesis of several new atropisomeric amino alcohols having 1‐phenyl‐1H‐pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single‐crystal X‐ray measurement. The consequences of the size of the N‐substituents on enantioinduction were examined by employing the enantioselective catalytic addition of diethylzinc to a series of substituted benzaldehydes (yields 91–97%, up to 85% enantiomeric excess). The special effect of the ortho methoxy group of the substrate on the enantioinduction is also interpreted. Chirality 27:216–222, 2015. © 2014 Wiley Periodicals, Inc.
Bibliography:	Supporting info item ArticleID:CHIR22415 istex:D7373F6DB72D15AD1ABEB74A27F459750E5664A8 ark:/67375/WNG-BHD49PJ4-C ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0899-0042 1520-636X
DOI:	10.1002/chir.22415