Asymmetric cross- and self-aldol reactions of aldehydes in water with a polystyrene-supported triazolylproline organocatalyst

Abstract

<p> <style type="text/css"> <!-- /* Font Definitions */ @font-face {font-family:"Cambria Math"; panose-1:2 4 5 3 5 4 6 3 2 4; mso-font-charset:0; mso-generic-font-family:auto; mso-font-pitch:variable; mso-font-signature:-536870145 1107305727 0 0 415 0;} @font-face {font-family:Calibri; panose-1:2 15 5 2 2 2 4 3 2 4; mso-font-charset:0; mso-generic-font-family:auto; mso-font-pitch:variable; mso-font-signature:-520092929 1073786111 9 0 415 0;} /* Style Definitions */ p.MsoNormal, li.MsoNormal, div.MsoNormal {mso-style-unhide:no; mso-style-parent:""; margin-top:0cm; margin-right:0cm; margin-bottom:10.0pt; margin-left:0cm; line-height:115%; mso-pagination:widow-orphan; font-size:11.0pt; font-family:Calibri; mso-ascii-font-family:Calibri; mso-ascii-theme-font:minor-latin; mso-fareast-font-family:Calibri; mso-fareast-theme-font:minor-latin; mso-hansi-font-family:Calibri; mso-hansi-theme-font:minor-latin; mso-bidi-font-family:"Times New Roman"; mso-bidi-theme-font:minor-bidi; mso-ansi-language:EN-GB;} p.RSCB01COMAbstract, li.RSCB01COMAbstract, div.RSCB01COMAbstract {mso-style-name:"RSC B01 COM Abstract"; mso-style-unhide:no; mso-style-qformat:yes; mso-style-link:"RSC B01 COM Abstract Char"; margin-top:0cm; margin-right:0cm; margin-bottom:10.0pt; margin-left:0cm; text-align:justify; line-height:12.0pt; mso-line-height-rule:exactly; mso-pagination:widow-orphan; font-size:9.0pt; mso-bidi-font-size:11.0pt; font-family:Calibri; mso-ascii-font-family:Calibri; mso-ascii-theme-font:minor-latin; mso-fareast-font-family:Calibri; mso-fareast-theme-font:minor-latin; mso-hansi-font-family:Calibri; mso-hansi-theme-font:minor-latin; mso-bidi-font-family:"Times New Roman"; mso-bidi-theme-font:minor-bidi; mso-ansi-language:EN-GB; mso-fareast-language:EN-GB; font-weight:bold; mso-bidi-font-weight:normal; mso-no-proof:yes;} span.06CHeading {mso-style-name:"06 C Heading"; mso-style-priority:1; mso-style-unhide:no; mso-ansi-font-size:9.0pt; mso-bidi-font-size:9.0pt; font-family:"Times New Roman"; mso-ascii-font-family:"Times New Roman"; mso-hansi-font-family:"Times New Roman"; mso-bidi-font-family:"Times New Roman"; font-variant:small-caps; mso-font-width:108%; font-weight:bold; mso-bidi-font-weight:normal;} span.RSCB01COMAbstractChar {mso-style-name:"RSC B01 COM Abstract Char"; mso-style-unhide:no; mso-style-locked:yes; mso-style-link:"RSC B01 COM Abstract"; mso-ansi-font-size:9.0pt; mso-fareast-language:EN-GB; font-weight:bold; mso-bidi-font-weight:normal; mso-no-proof:yes;} .MsoChpDefault {mso-style-type:export-only; mso-default-props:yes; font-size:11.0pt; mso-ansi-font-size:11.0pt; mso-bidi-font-size:11.0pt; font-family:Calibri; mso-ascii-font-family:Calibri; mso-ascii-theme-font:minor-latin; mso-fareast-font-family:Calibri; mso-fareast-theme-font:minor-latin; mso-hansi-font-family:Calibri; mso-hansi-theme-font:minor-latin; mso-bidi-font-family:"Times New Roman"; mso-bidi-theme-font:minor-bidi; mso-ansi-language:EN-GB;} .MsoPapDefault {mso-style-type:export-only; margin-bottom:10.0pt; line-height:115%;} @page WordSection1 {size:612.0pt 792.0pt; margin:72.0pt 90.0pt 72.0pt 90.0pt; mso-header-margin:36.0pt; mso-footer-margin:36.0pt; mso-paper-source:0;} div.WordSection1 {page:WordSection1;} --> </style> </p> <p class="RSCB01COMAbstract"> <span class="06CHeading"><span lang="EN-GB" style="font-weight:normal">A polystyrene-immobilized triazolylproline has been prepared by a bottom-up approach involving co-polymerization with full regiocontrol. The resulting PS resin swells in water and has been applied to the enantioselective cross-aldol reaction and to the self-aldol reaction of aldehydes under essentially neat conditions, excellent yields and stereoselectivities being recorded.</span></span></p>