Volume 16, Fiesers' Reagents for Organic Synthesis by Mary Fieser

By Mary Fieser

This quantity is a part of a continual sequence which defines and demonstrates the guidance, homes and makes use of of reagents. The publication surveys the literature released at the topic from mid-1989 to the start of 1991.

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The desiredsyn. ,, ^,, BF"o(c':' -, | ^,,,r\,rtnr LHr 84% ( syn-2 + anti-2 , 20:80 CH, (E)-1 by a methyl andhigheryields' Since(Z)- and(E)-1differ only ofdiastereoselectivity, of (Z)- and stereoselectivity intrinsic substituent,their behavior sliouldreflect the (E)-enols. bc t-butyldimethylsilyl ether and Bl eren reverse the aldehyde diastereol V. A. Ciufolini and G. O. J. ' Y. Yamamotoand M. t J S. Panekand M. A. Sparks,J. Ory' S D. ,54,49t2 (19 ' S Yamago,D. Machii, and E. Nrlrr ' C H. Heathcockand L.

XDs ( )-cHo \_J ' r I E. Markd, A. Mekhaltu. r i E. Markd and A. Mekhrll N-Bromosuccinimide 49 9-Bromo-9-phenylfluorene, 13, 48-49. r rT. F. Jamison, W. D. Lubell,J. M. Dener,M. J. Krischd, andH. Rapoport, Org. , (1990). submitted in 'sr,11ns with C2H5MgBr ! r(\ \rbtainfour stereoisoof the ollrngthegeometry chelabY grouP cart'r-nyl cctedfrom the (Z)-lithium r methyl grouPso to the ngnesiumenolate,which N-Bromosuccinimide. r primary benzylicsilyl ethersare oxidizedby NBScatalyzedby AIBN to thecorresponding aldehydesin70-87% yield.

3 Hydrogenationof the cyclic p-keto ester 2 catalyzedby an (R)-BINAP-Rucomplex(l) proceedswith high dnti-diastereoselecof rivity to give a 99 : I mixtureof 3 and4. On theotherhand,catalytichydrogenation rhe acyclic keto ester 5a proceedswith no appreciableresolutionto give a l: I o o H i l | ;\-coocH',*,-r,^1, ---;;- *u,,, /}"'coocH' \-J \J 3, (lR, 2R), 927o ee lrldrng ; . *r'cH3 I 91% coocHs si, 4 , ( l R , 2 S ) , 9 3 7 oe e mixtur€of syn- andanti-6. In theseasymmetrichydrogenations, Cr is determinedby the chirality of the BINAP ligand and the C2 configuration Jependson the substrate.

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