Stereodivergent synthesis of optically active tertiary alcohols via addition reaction of chiral 2-acyl oxazolidine with organometallics

1991 ◽  
Vol 32 (25) ◽  
pp. 2919-2922 ◽  
Author(s):  
Yutaka Ukaji ◽  
Kouji Yamamoto ◽  
Masashi Fukui ◽  
Tamotsu Fujisawa
Keyword(s):  
Addition Reaction ◽  
Optically Active ◽  
Tertiary Alcohols

Synthesis of optically active tellurium-containing binaphthyls and their use in the asymmetric 1,4-addition reaction of α,β-unsaturated ketones

1993 ◽  
Vol 4 (10) ◽  
pp. 2127-2130 ◽  
Author(s):  
Masaki Irie ◽  
Yoshitaka Doi ◽  
Masahiro Ohsuka ◽  
Yoshio Aso ◽  
Tetsuo Otsubo ◽  
...  
Keyword(s):  
Addition Reaction ◽  
Optically Active ◽  
Unsaturated Ketones

scholarly journals General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors

2020 ◽  
Author(s):  
Roger Machín Rivera ◽  
Yujin Jang ◽  
Christopher M. Poteat ◽  
Vincent Lindsay
Keyword(s):  
Optically Active ◽  
Organometallic Reagents ◽  
Tertiary Alcohols ◽  
Mild Conditions ◽  
Synthetic Approaches ◽  
General Synthesis

The addition of organometallic reagents to ketones constitutes one of the most straightforward synthetic approaches to tertiary alcohols. However, due to the absence of a well-behaved class of cyclopropanone surrogates accessible in enantioenriched form, such a trivial synthetic disconnection has only received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we report a simple and high-yielding synthesis 1-substituted cyclopropanols via the addition of diverse organometallic reagents to 1- phenylsulfonylcyclopropanols, acting here as in situ precursors of the corresponding cyclopropanones.The transformation is shown to be amenable to sp, sp2 or sp3 -hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions and the formation of optically active cyclopropanols.

Biocatalytic synthesis of optically active tertiary alcohols

2011 ◽  
Vol 91 (3) ◽  
pp. 505-517 ◽  
Author(s):  
Robert Kourist ◽  
Uwe T. Bornscheuer
Keyword(s):  
Optically Active ◽  
Tertiary Alcohols
Sign in / Sign up

Export Citation Format

Share Document