Chemistry Reference
In-Depth Information
ACKNOWLEDGMENTS
We thank the NIH (Grant GM-59426) and the NSF (Grants CHE-0213009 and CHE-
0715138) for support of our programs in catalytic olefi n metathesis. We are most
grateful to Professor Richard R. Schrock and his coworkers who have collaborated
with us since 1997 in connection with the development of Mo-based catalysts for
enantioselective olefi n metathesis. Finally, we particularly acknowledge the intellectual
and experimental contributions of our former coworkers, J. S. Kingsbury, S. B. Garber,
J. J. Van Veldhuizen, D. G. Gillingham, O. Kataoka, G. S. Weatherhead, J. A.
Jernelius, E. S. Sattely, S. J. Dolman, G. A. Cortez, A. Puglisi, A.-L. Lee, C. A. Baxter,
and D. C. Moebius.
REFERENCES
1. (a) Grubbs , R. H. (Ed.).
Handbook of Metathesis
. Weinheim : Wiley - VCH , 2003 . (b) Zhugralin , A.
R. ; Hoveyda , A. H.
Nature
2007
,
450
, 243 - 251 . (c) Nicolaou , K. C. ; Bulger , P. G. ; Sarlah , D.
Angew.
Chem. Int. Ed.
2005
,
44
, 4490 - 4527 .
2. (a) Dolman , S. J. ; Hultzsch , K. C. ; Pezet , F. ; Teng , X. ; Hoveyda , A. H. ; Schrock , R. R.
J. Am. Chem.
Soc.
2004
,
126
, 10945-10953. For an earlier disclosure of chiral Mo-diolate catalysts on a different
solid support, see: (b) Hultzsch , K. C. ; Jernelius , J. A. ; Hoveyda , A. H. ; Schrock , R. R.
Angew. Chem.
Int. Ed.
2002
,
41
, 589 - 593 .
3. For a review of desymmetrization processes, see: (a) Willis , M. C.
J. Chem. Soc. Perkin Trans. 1
1999
, 1765-1784. Additionally, a number of other enantioselective transformations, where the
stereochemical outcome is controlled indirectly through desymmetrization, have been reported.
For Wittig - type reactions, see: (b) Rein , T. ; Pedersen , T. M.
Synthesis
2002
, 579 - 594 . (c) Lertpibul-
panya , D. ; Marsden , S. P. ; Rodriguez - Garcia , I. ; Kilner , C. A.
Angew. Chem. Int. Ed.
2006
,
45
,
5000 - 5002 . (d) Headley , C. E. ; Marsden , S. P.
J. Org. Chem.
2007
,
72
, 7185 - 7189 . For oxidation of
meso - diols, see: (e) Ferreira , E. M. ; Stoltz , B. M.
J. Am. Chem. Soc.
2001
,
123
, 7725 - 7726 . (f) Mandal ,
S. K. ; Sigman , M. S.
J. Org. Chem.
2003
,
68
, 7535 - 7537 . (g) Suzuki , T. ; Morita , K. ; Matsuo , Y. ; Hiroi ,
K .
Tetrahedron Lett.
2003
,
44
, 2003 - 2006 . (h) Shimizu , H. ; Onitsuka , S. ; Egami , H. ; Katsuki , T.
J.
Am. Chem. Soc.
2005
,
127
, 5396 - 5413 . (i) Onumura , O. ; Arimoto , H. ; Matsumura , Y. ; Demizu , Y .
Tetrahedron Lett.
2007
,
48
, 8668 - 8672 . For silylation of meso - diols, see: (j) Zhao , Y. ; Rodrigo , J. ;
Hoveyda , A. H. ; Snapper , M. L.
Nature
2006
,
443
, 67 - 70 . For enantioselective acylation and phos-
phorylation reactions, see: (k) Miller , S. J.
Acc. Chem. Res.
2004
,
37
, 601 - 610 . For enantioselective
Baeyer - Villiger reactions, see: (l) Xu , S. ; Wang , Z. ; Zhang , X. ; Zhang , X. ; Ding , K.
Angew. Chem.
Int. Ed.
2008
,
47
, 2840-2843 and references cited therein. For an enantioselective Schmidt reaction,
see: (m) Ribelin , T. ; Katz , C. E. ; English , D. G. ; Smith , S. ; Manukyan , A. K. ; Day , V. W. ; Neuen-
swander , B. ; Poutsma , J. L. ; Aub é , J.
Angew. Chem. Int. Ed.
2008
,
47
, 6233 - 6235 . For ring opening
of cyclic meso - anhydrides, see: (n) Spivey , A. C. ; Andrews , B. I.
Angew. Chem. Int. Ed.
2001
,
40
,
3131 - 3134 .
4. (a) Schrock , R. R. ; Hoveyda , A. H.
Angew. Chem. Int. Ed.
2003
,
42
, 4592 - 4633 . (b) Hoveyda , A. H. ;
Gillingham , D. G. ; Van Veldhuizen , J. J. ; Kataoka , O. ; Garber , S. B. ; Kingsbury , J. S. ; Harrity , J. P.
A.
Org. Biomol. Chem.
2004
,
2
, 8 - 23 .
5. Seiders , T. J. ; Ward , D. W. ; Grubbs , R. H.
Org. Lett.
2001
,
3
, 3225 - 3228 .
6. For enantioselective RCM promoted by Ru - based chiral catalysts, see: (a) Van Veldhuizen , J. J. ;
Gillingham , D. G. ; Garber , S. B. ; Kataoka , O. ; Hoveyda , A. H.
J. Am. Chem. Soc.
2003
,
125
, 12502 -
12508 . (b) Funk , T. W. ; Berlin , J. M. ; Grubbs , R. H.
J. Am. Chem. Soc.
2006
,
128
, 1840 - 1846 . (c)
Fournier , P. - A. ; Collins , S. K.
Organometallics
2007
,
26
, 2945 - 2949 . (d) Funk , T. W.
Org. Lett.
2009
,
11
, 4998 - 5001 . For related transformations, promoted by Mo - based complexes, see: (e) La , D. S. ;
Alexander , J. B. ; Cefalo , D. R. ; Graf , D. D. ; Hoveyda , A. H. ; Schrock , R. R.
J. Am. Chem. Soc.
1998
,
