{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T19:19:46Z","timestamp":1790968786636,"version":"4.1.0"},"reference-count":117,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2009,5,5]],"date-time":"2009-05-05T00:00:00Z","timestamp":1241481600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2009,6,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    <jats:bold>Asymmetric catalysis<\/jats:bold>\n                    : A facile enantioselective Strecker reaction of ketimines with trimethylsilyl cyanide (TMSCN) was realized by employing chiral (\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010BNPNa\n                    <jats:bold>3\u2009e<\/jats:bold>\n                    and PBAP as an additive (see image). A wide substrate scope and good\u2010to\u2010excellent enantioselectivities were achieved.\n                    <jats:boxed-text content-type=\"graphic\" position=\"anchor\">\n                      <jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\">\n                        <jats:alt-text>magnified image<\/jats:alt-text>\n                      <\/jats:graphic>\n                    <\/jats:boxed-text>\n                  <\/jats:p>\n                  <jats:p>\n                    A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali\u2010metal salt has been developed. When 10\u2005mol\u2009% BNPNa (BNP=1,1\u2032\u2010binaphthyl\u20102,2\u2032\u2010diylphosphate) prepared in situ and 10\u2005mol\u2009%\n                    <jats:italic>para<\/jats:italic>\n                    \u2010\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010butyl\u2010\n                    <jats:italic>ortho<\/jats:italic>\n                    \u2010adamantylphenol (PBAP) were introduced into the reaction, up to 96\u2009% yield and up to 95\u2009%\u2005\n                    <jats:italic>ee<\/jats:italic>\n                    (\n                    <jats:italic>ee<\/jats:italic>\n                    =enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from \u03b2\u2010acetonaphthone, \u03b1\u2010indanone, and \u03b1\u2010tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1\u2032\u2010binaphthyl\u20102,2\u2032\u2010diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.\n                  <\/jats:p>","DOI":"10.1002\/chem.200900210","type":"journal-article","created":{"date-parts":[[2009,5,5]],"date-time":"2009-05-05T12:31:17Z","timestamp":1241526677000},"page":"6008-6014","source":"Crossref","is-referenced-by-count":106,"title":["Facile and Efficient Enantioselective Strecker Reaction of Ketimines by Chiral Sodium Phosphate"],"prefix":"10.1002","volume":"15","author":[{"given":"Ke","family":"Shen","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaohua","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yunfei","family":"Cai","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lili","family":"Lin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoming","family":"Feng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,5,29]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For reviews on the asymmetric Strecker reaction 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[2i]."},{"key":"e_1_2_6_74_2","unstructured":"The water or methanol generated in situ from3\u2009eand NaOH or NaOMe respectively might interfere in the reaction. The insufficient basicity of Na2CO3might cause inadequate formation of sodium salt."},{"key":"e_1_2_6_75_2","unstructured":"Reviews on chiral Br\u00f8nsted acids:"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068374j"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200606074"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200600529"},{"key":"e_1_2_6_78_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600529"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200503132"},{"key":"e_1_2_6_79_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503132"},{"key":"e_1_2_6_80_2","first-page":"348","author":"Akiyama T.","year":"2006","journal-title":"Adv Synth. Catal."},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460394"},{"key":"e_1_2_6_81_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460394"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500154"},{"key":"e_1_2_6_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500154"},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200301732"},{"key":"e_1_2_6_83_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200301732"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1039\/b107298f"},{"key":"e_1_2_6_85_2","unstructured":"The unexpected reversal of the absolute enantioselectivity is not fully understood and further examinations are necessary. However not only steric and electric factors but also the repulsion between 3 3\u2032\u2010substituents of the BINOL skeleton and the bulky Dpp group of1\u2009ashould be involved."},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00368a030"},{"key":"e_1_2_6_87_2","unstructured":"\u00a0"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0300439"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00979a009"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60274a003"},{"key":"e_1_2_6_91_2","unstructured":"A negative nonlinear effect (NLE) was observed in the absence of PBAP and a proposed dimer species is described in the Supporting Information. 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