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The roles of the stereogenic center at the aminophosphane phosphorus atom (NP*) and of the chirality of the backbone were analyzed by considering three experimentally tested cases: 1) P\u2010stereogenic yielding high <jats:italic>ee<\/jats:italic>, 2) P\u2010nonstereogenic yielding low <jats:italic>ee<\/jats:italic>, and 3) P\u2010stereogenic yielding low <jats:italic>ee<\/jats:italic>. We succeeded in reproducing the experimentally observed trends for the three studied AMPP ligands. Our results indicated that alkene insertion into the rhodium\u2013hydride bond is the selectivity\u2010determining step, and not alkene coordination. Additional calculations on model systems revealed that the different nonbonding weak\u2010type interactions of styrene with the substituents of the NP* stereogenic center in an axial position is responsible for stereodifferentiation. The chirality of the AMPP backbone plays a secondary role. The rationalization of the stereochemical outcome is not straightforward, because two competitive equatorial\/axial reaction paths, showing opposite asymmetric induction, must be considered. Construction of stereochemical models and evaluation of stereoinduction for novel ligand systems suggested that two prerequisites are required to improve the performance of AMPP\u2010type ligands in asymmetric hydroformylation: 1) combination of stereorecognition and stereohindrance by substituents at the NP* atom, and 2) more rigid backbones.<\/jats:p>","DOI":"10.1002\/chem.200500606","type":"journal-article","created":{"date-parts":[[2005,11,28]],"date-time":"2005-11-28T13:18:56Z","timestamp":1133183936000},"page":"1457-1467","source":"Crossref","is-referenced-by-count":36,"title":["Origin of Stereoinduction by Chiral Aminophosphane Phosphinite Ligands in Enantioselective Catalysis: Asymmetric Hydroformylation"],"prefix":"10.1002","volume":"12","author":[{"given":"Jorge J.","family":"Carb\u00f3","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Agust\u00ed","family":"Lled\u00f3s","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dieter","family":"Vogt","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Carles","family":"Bo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2006,1,23]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471721506"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-58571-5"},{"key":"e_1_2_6_4_2","volume-title":"Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals,","author":"Fu G. 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