Rationalization of the stereochemistry of an addition of dialkyl phosphites to certain chiral aldimines: The experimental and theoretical approach | Zendy

Nazarski Ryszard B. | Zendy; Lewkowski Jarosław A. | Zendy; Skowroński Romuald | Zendy

Open Access

Rationalization of the stereochemistry of an addition of dialkyl phosphites to certain chiral aldimines: The experimental and theoretical approach

Author(s) -

Nazarski Ryszard B.,

Lewkowski Jarosław A.,

Skowroński Romuald

Publication year - 2002

Publication title -

heteroatom chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.283

H-Index - 42

eISSN - 1098-1071

pISSN - 1042-7163

DOI - 10.1002/hc.10005

Subject(s) - chemistry , stereocenter , heteroatom , mndo , diastereomer , furfural , alkane stereochemistry , aldimine , computational chemistry , stereochemistry , organic chemistry , enantioselective synthesis , crystal structure , catalysis , molecule , alkyl

The absolute configuration of an α‐P stereogenic center in two diastereomeric O,O‐dialkyl α‐aminophosphonates ( 3 ), arising from an induced 1,3‐asymmetric phosphite addition to the CN bond of furfural‐derived Schiff bases ( 1 ), was established from single product 1 H NMR data. Such spectra were interpreted with anisotropic shielding in relation to the AM1 and MNDO/d structures of 3 ; the former ones turned out to be closer to the obtained experimental results ( 1 H NMR spectra of 3 , crystallographic database study). Since favored 3‐21G geometries of starting imines 1 were modeled as well, it was inferred that a stereochemical outcome of this reaction is governed by Cram selectivity. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:120–125, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10005

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research