Organic Reactions, Volume 73 by Scott E. Denmark PDF

By Scott E. Denmark

ISBN-10: 0470436905

ISBN-13: 9780470436905

For all volumes: the volumes of natural Reactions are collections of chapters each one dedicated to a unmarried response or a definitive part of a response, of large applicability. The authors have had event with the techniques surveyed. the themes are awarded from the preparative standpoint and specific recognition is given to boundaries, interfering impacts, results of constitution and the choice of experimental thoughts. each one bankruptcy comprises numerous specified systems illustrating the numerous adjustments of the tactic. each one bankruptcy includes pills that come with all of the examples of the response into consideration that the writer has been capable of finding.

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Organic Reactions, Volume 73 - download pdf or read online

For all volumes: the volumes of natural Reactions are collections of chapters every one dedicated to a unmarried response or a definitive section of a response, of broad applicability. The authors have had event with the strategies surveyed. the topics are provided from the preparative point of view and specific cognizance is given to obstacles, interfering affects, results of constitution and the choice of experimental concepts.

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166 Both examples involving aldehyde 39 (Eqs. 82 and 83) are very favorable in comparison to the modest selectivity of the achiral pinacol allylboronates (compare to Scheme 2). Reagent control is observed even in mismatched situations such as the difficult case of α-phenyl aldehyde 115 (Eq. 166,167 B[(+)-Ipc]2 64 OH OH + (Eq. r. H B[(–)-Ipc]2 64 39 OH OH + (Eq. r. B[(+)-Ipc]2 64 OH (Eq. r. H Ph 115 OH B[(–)-Ipc]2 64 OH OH + (Eq. r. 44 ORGANIC REACTIONS By using a judicious combination of the appropriate double bond geometry and pinene enantiomer, the corresponding crotylboranes present a very nice solution to the problem of full stereocontrol of acyclic dipropionate units when combined with chiral α-methyl β-alkoxy aldehydes such as 116 (Eqs.

The competing transition structure with the pseudo-equatorial substituent would experience severe non-bonding interactions between this group and the bulky boronic ester moiety. S. Cy + RCHO R = Et (79%) 98% ee R = Ph (71%) 99% ee Cy 21 O B O R OH Cy R O 84 83 Scheme 9. Stereoinduction model for the additions of chiral α-methyl crotylboronate 21. 36 ORGANIC REACTIONS R R O B O R PhCHO, toluene R –100° to rt O O B O H CO2Et OH Ph 86 (91%) 96% ee CO2Et 29 R = CPh2(OMe) CO2Et Ph 85 (Eq. 63) Recently, the first examples of catalytic enantioselective preparations of chiral α-substituted allylic boronates have appeared.

2 eq), 4 Å MS, CH2Cl2, –78°, 2 h HO (Eq. 164 One such example is shown in Eq. 81. On the basis of 11 B NMR experiments and on the lack of diastereoselectivity in crotylation reactions, the ALLYLBORATION OF CARBONYL COMPOUNDS 43 mechanism of this allylation is believed to involve transmetalation of the boron to an allylcopper species. O O B + CuF2•2H2O (3 mol%), (R,R)-i-Pr-DUPHOS (6 mol%) OH (Eq. 165 The most desirable situation is where there is very high reagent control to override the intrinsic effect of the stereogenic center of the aldehyde or ketone on the diastereofacial selectivity.

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Organic Reactions, Volume 73 by Scott E. Denmark


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