114341-71-8Relevant academic research and scientific papers
Highly stereoselective construction of the C2 stereocentre of α-tocopherol (Vitamin E) by asymmetric addition of Grignard reagents to ketones
Bieszczad, Bartosz,Gilheany, Declan G.
, p. 6483 - 6492 (2017/08/16)
Tertiary alcohol precursors of both C2 diastereoisomers of α-tocopherol were prepared in three ways by our recently reported asymmetric Grignard synthesis. The versatility of Grignard chemistry inherent in its three-way disconnection was exploited to allow the synthesis of three product grades: 77:23 dr (5 steps), 81:19 dr (5 steps) and 96:4 dr (7 steps, one gram scale) from readily available and abundant starting materials. The products were converted to their respective α-tocopherols in 3 steps, which allowed a definitive re-assignment of their absolute configurations.
Total synthesis of (R, R, R)-γ-tocopherol through cu-catalyzed asymmetric 1,2-addition
Wu, Zhongtao,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.
supporting information, p. 14250 - 14255 (2015/03/18)
Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R, R, R)-γ-tocopherol has been synthesized in 36% yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73% ee by the 1,2-addition of a phytol-derived Grignard reagent to an a-bromo enone prepared from 2,3-dimethylquinone.
Chromanemelonate esters
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, (2008/06/13)
Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.
2-allylchromans
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, (2008/06/13)
Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.
2-halochromans
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, (2008/06/13)
Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.
