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On the diastereoselectivity of cyanide addition to β-hydroxyketones: One-pot synthesis of syn β-hydroxycyanohydrins and anti 2,4-dihydroxyamides by Manohar Singh Batra; Francisco J. Aguilar; Ernesto Brunet is a Chemistry article available to read on EtoBox.

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LJepartamemo de Q&&a. C-I. Foculul de Cienciaa. lJniversi&d Aut&wma &Madrid. 2&W-Madrid (Spain). FAX MI-3973966 Ah&act. Theiatrinaic stereuel~tivity of the cyxnide xddition to p-hydroxyketoaea in the presence of 18cnmmb or zaI2 ill lower than that pmviollxly lqortai. How8ver, the lestion bears a pmctical vxlue in thxt syn ~-hyd~~xycyxaohydri~ xnd onri 2,4dihydfoxyxmidf~3 can be dixsWea&ctively obtaiwd in mxnonxble yielda in wme-pot pmcedum. The high d.e.'s initixlly repted we-m due to the work-up proccdw, where the I-ICI cawcrted much fister the anri p-hydmxycyxnohydrin thxn the syn productintothecorrsspoadinO~.ThishstsrcoovsreionisexplPinedin~ofmchimeric xs&&nce of ~-hydroxyl group. Details xre givm xs to the umf1gumtional4gnmmt of products by 2D NMR alld mDlecldar mechanic& IdFOdUCtIOIl The stereoselective production of 1,3diols has attmcted much attention in recent years because this functionality is recurrently present in a great variety of important natural products.2 Synthesis of 1,3diols may be achieved by addition of nuclophiles to g-hydroxyaldehydes or ketrnu~.~ Reduction of the latter compounds has been thoroughly studied and it can be directed to produce either syn or an

Who reads On the diastereoselectivity of cyanide addition to β-hydroxyketones: One-pot synthesis of syn β-hydroxycyanohydrins and anti 2,4-dihydroxyamides?

Author

Manohar Singh Batra; Francisco J. Aguilar; Ernesto Brunet

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1994

Language

EN

Field

Chemistry (Physical Sciences)