An Especially Convenient Stereoselective Reduction of β-Hydroxy Ketones to Anti 1,3 Diols Using Samarium Diiodide†

1999 ◽  
Vol 64 (7) ◽  
pp. 2172-2173 ◽  
Author(s):  
Gary E. Keck ◽  
Carrie A. Wager ◽  
Thorsten Sell ◽  
Travis T. Wager
Keyword(s):  
Samarium Diiodide ◽  
Stereoselective Reduction ◽  
Hydroxy Ketones

ChemInform Abstract: An Especially Convenient Stereoselective Reduction of β-Hydroxy Ketones to anti 1,3 Diols Using Samarium Diiodide.

ChemInform ◽  
2010 ◽  
Vol 30 (32) ◽  
pp. no-no
Author(s):  
Gary E. Keck ◽  
Carrie A. Wager ◽  
Thorsten Sell ◽  
Travis T. Wager
Keyword(s):  
Samarium Diiodide ◽  
Stereoselective Reduction ◽  
Hydroxy Ketones

Stereoselective Reduction of β-Hydroxy Ketones with AldehydesviaTishchenko Reactions Catalyzed by Zirconocene Complexes1

1997 ◽  
Vol 62 (10) ◽  
pp. 3409-3412 ◽  
Author(s):  
Yuuji Umekawa ◽  
Satoshi Sakaguchi ◽  
Yutaka Nishiyama ◽  
Yasutaka Ishii
Keyword(s):  
Stereoselective Reduction ◽  
Hydroxy Ketones

Synthesis and Characterisation of Bridged Morpholine Derivatives Fused to a Phenanthrene Ring System

2017 ◽  
Vol 41 (4) ◽  
pp. 210-215 ◽  
Author(s):  
H. Surya Prakash Rao ◽  
Satish Vijjapu
Keyword(s):  
Spectral Analysis ◽  
Ring System ◽  
Optically Active ◽  
Theoretical Studies ◽  
Stereoselective Reduction ◽  
Steric Interactions ◽  
Conformationally Restricted ◽  
Hydroxy Ketones ◽  
Morpholine Derivatives

The synthesis of conformationally restricted and facially biased bridged morpholine derivatives fused to a phenanthrene ring system was prepared in a three-step sequence involving: (i) Voight rearrangement; (ii) stereoselective reduction of ketone and (iii) iodine mediated cyclisation, the α-allyl-α-hydroxy-ketones gave the corresponding bridged N-substituted morpholines. One of the bridged morpholine derivatives fused to a phenanthrene ring system was optically active. The NMR spectral analysis and theoretical studies show that substitution on nitrogen prefers exo-orientation, possibly to avoid steric interactions with the phenanthrene moiety.

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