CHEMISTRY 534 FALL 2013 HYDRIDE REDUCTION

I. General A. Carey and Sundberg: Part B, Ch. 4, pp 226-240; 262-290 (5th Ed. Ch. 4, pp 337-353, Ch. 5,

pp 396-425) B. Carruthers and Coldham: Ch. 7, pp 434-454 B. Gawley and Aube: Ch. 7, pp 294-316; 317-321 II. Reviews A. N. Greeves in Comprehensive Organic Synthesis, Vol. 8, Reduction, I. Fleming, Ed.; Pergamon

Press, 1991; pp 1-24. A. G. M. Barrett, Ibid. pp 236-257. R. A. W. Johnstone, Ibid. pp 259-281.

B. J. Seyden-Penne, Reductions by the Alumino and Borohydrides in Organic Synthesis; VCH, 1991

C. M. N. Rerick in Reduction, R. L. Augustine, Ed.; Marcel Dekker, 1960; Ch. 1 D. H. C. Brown, Tetrahedron 1979, 35, 567

III. Stereochemistry and Mechanism

A. D. C. Wigfield, Tetrahedron 1979, 35, 449 B. E. C. Ashby, Top. Stereochem. 1979, 11, 53 C. A. S. Cieplak, Chem Rev. 1999, 99, 1265 D. T. Nakata, Acc. Chem. Res. 1984, 17, 338 E. K. Houk in Stereochemistry of Organic and Bioorganic Transformations, W. Bartmann and K.

Sharpless, Eds.; Verlag Chemie, 1986; p 247

IV. Selected Reagents A. Trialkylborohydrides: Aldrichimica Acta 1974, 7, l55; Gribble, Org. Proc. Res. Dev. 2006, 10,

1062. B. Trialkoxyaluminohydrides: J. Org. Chem. 1981, 46, 4629; Org. React. 1985, 34, 1; Org.

React. 1988, 36, 249 C. Diisobutylaluminum Hydride: J. J. Eisch, in Comprehensive Organic Synthesis, Vol. 8, I.

Fleming, Ed.; Pergamon Press, 1991; pp 733-761 Org. React. 1984, 32, 375 Synthesis 1975, 617 D. Sodium Cyanoborohydride: Org. Prep. Proc. Int. 1979, 11, 201; Org. Prep. Proc. Int. 1985, 17,

317 E. Aluminum Alkoxides: Org. React. 1944, 2, 178 F. Tributyltin Hydride: W. P. Neumann Synthesis 1987, 665. P. Caubere Angew. Chem Int. Ed.

Engl. 1983, 22, 599 G. Silicon Hydrides: G. R. Larson; J. L. Fry Org. React. 2007, 71, 1.

V. Directed Hydride Reductions

A. General: Asymmetric Organic Reactions, American Chemical Society, 1980, Ch. 3 B. 1,2-Induction: 1. α-alkyl: Midland,: J. Am. Chem. Soc. 1983, 105, 3725 Tsuchihashi: Tetrahedron Lett. 1984, 25, 2479 Yamaguchi, Tetrahedron Lett. 1985, 26, 4643 Brown, J. Chem. Soc., Chem. Commun. 1985, 455 2. α−hetero: Hiyama: J. Am. Chem. Soc. 1984, 106, 4629 Overman: Tetrahedron Lett. 1982, 23, 2355 Shimogaki: Tetrahedron Lett. 1984, 25, 4775 C. 1,3-Induction: 1. β−hydroxy-ketone: Narasaka: Chem. Lett. 1980, 1415 Chen: Tetrahedron Lett. 1987, 28, 155 Evans: Tetrahedron Lett. 1986, 27, 5939 Evans: J. Am. Chem. Soc. 1988, 110, 3560

VI. Asymmetric Reduction Methods A. Reviews: 1. Chiral Hydrides; M. Nishizawa and R. Noyori in Comprehensive Organic Synthesis, Vol. 8,

Reduction, I. Fleming, Ed.; Pergamon Press, 1991; pp 159-182 2. Enzymatic Reduction; J. B. Jones, Ibid.; pp183-209. 3. Dihydropyridines; R. M. Kellogg, Ibid., pp 79-106. B. Boron: Hydroboration: Asymmetric Synthesis; Academic Press, 1983; Vol. 2, Ch. 1, 2 Chem. Rev. 1989, 89, 1553 Accounts Chem. Res. 1992, 25, 16 Tetrahedron 1981, 37, 3547 C. Aluminum: Top. Stereochem. 1983, 14, 231 Asymmetric Synthesis; Academic Press, 1983; Vol. 2, Ch. 3 D. Dihydropyridines: Studies in Organic Chemistry; Amsterdam, 1983, 135 Asymmetric Synthesis; Academic Press, 1983; Vol. 2, Ch. 4 VII. Catalytic Reductions A. Reviews: 1. Boron: a. S. Itsuno in Comprehensive Asymmetric Catalysis, Vol. I, E. N. Jacobsen, A. Pfaltz

and H. Yamamoto, Eds.; Springer Verlag, 1999, Ch. 6.4, pp 289-315 b. E. J. Corey, Angew. Chem., Int. Ed. 1998, 37, 1987. c. S. Istuno, Org. React. 1998, 52, 395 c. V. A. Glushkov, Russ. Chem. Rev. 2004, 73, 581. d. K. Matos, Chem. Rev. 2006, 106, 2617 2. Silicon: a. T. Hayashi in Comprehensive Asymmetric Catalysis, Vol. I-III; Jacobsen, E. N.;

Pfaltz, A.; Yamamoto, H., Eds.; Springer Verlag: Heidelberg, 1999, Ch. 7. b. H. Nishiyama; K. Itoh in Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.

Chapt. 2. B. Itsuno: J. Org. Chem. 1984, 49, 555 J. Chem. Soc., Perkin Trans 1,1985, 2615 Bull. Chem. Soc. Jpn. 1987, 60, 395 C. Corey: J. Am. Chem. Soc. 1987, 109, 5551, 7925 D. Merck: J. Org. Chem. 1991, 56, 751; Mathre, J. Org. Chem. 1993, 58, 2881.