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Synthesis of (R)- and (S)-Allyloxiranes via Enantioselective Allylboration of Bromoacetaldehyde. Transformation of (R)-Allyloxirane into (–)-(R)-GABOB (GABOB = γ-amino-β-hydroxybutyric acid)

Yurii Nikolaevich Bubnov 1
Yurii Nikolaevich Bubnov
, 
Larisa I Lavrinovich 1
Larisa I Lavrinovich
, 
Andrei Yu Zykov 1
Andrei Yu Zykov
, 
Anatolii Victorovich Ignatenko 1
Anatolii Victorovich Ignatenko
10.1070/MC1992v002n03ABEH000145
Published 1992-09-30
Communication , Volume 2, Issue 3, 86-88
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Bubnov Y. N. et al. Synthesis of (R)- and (S)-Allyloxiranes via Enantioselective Allylboration of Bromoacetaldehyde. Transformation of (R)-Allyloxirane into (–)-(R)-GABOB (GABOB = γ-amino-β-hydroxybutyric acid) // Mendeleev Communications. 1992. Vol. 2. No. 3. pp. 86-88.
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Bubnov Y. N., Lavrinovich L. I., Zykov A. Yu., Ignatenko A. V. Synthesis of (R)- and (S)-Allyloxiranes via Enantioselective Allylboration of Bromoacetaldehyde. Transformation of (R)-Allyloxirane into (–)-(R)-GABOB (GABOB = γ-amino-β-hydroxybutyric acid) // Mendeleev Communications. 1992. Vol. 2. No. 3. pp. 86-88.
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TY - JOUR
DO - 10.1070/MC1992v002n03ABEH000145
UR - https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000145
TI - Synthesis of (R)- and (S)-Allyloxiranes via Enantioselective Allylboration of Bromoacetaldehyde. Transformation of (R)-Allyloxirane into (–)-(R)-GABOB (GABOB = γ-amino-β-hydroxybutyric acid)
T2 - Mendeleev Communications
AU - Bubnov, Yurii Nikolaevich
AU - Lavrinovich, Larisa I
AU - Zykov, Andrei Yu
AU - Ignatenko, Anatolii Victorovich
PY - 1992
DA - 1992/09/30
PB - Mendeleev Communications
SP - 86-88
IS - 3
VL - 2
ER -
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@article{1992_Bubnov,
author = {Yurii Nikolaevich Bubnov and Larisa I Lavrinovich and Andrei Yu Zykov and Anatolii Victorovich Ignatenko},
title = {Synthesis of (R)- and (S)-Allyloxiranes via Enantioselective Allylboration of Bromoacetaldehyde. Transformation of (R)-Allyloxirane into (–)-(R)-GABOB (GABOB = γ-amino-β-hydroxybutyric acid)},
journal = {Mendeleev Communications},
year = {1992},
volume = {2},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000145},
number = {3},
pages = {86--88},
doi = {10.1070/MC1992v002n03ABEH000145}
}
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Bubnov, Yurii Nikolaevich, et al. “Synthesis of (R)- and (S)-Allyloxiranes via Enantioselective Allylboration of Bromoacetaldehyde. Transformation of (R)-Allyloxirane into (–)-(R)-GABOB (GABOB = γ-amino-β-hydroxybutyric acid).” Mendeleev Communications, vol. 2, no. 3, Sep. 1992, pp. 86-88. https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000145.

Abstract

Enantioselective allylboration of bromoacetaldehyde with allyl(diisopinocampheyl)borane 2 or allyl(diisocaranyl)borane 3 has been used as a key step in the first synthesis of (+)-(R)-6 [89% enantiomeric excess (e.e.)] and (–)-(S)-allyloxirane 7 (92% e.e.), respectively; in two steps, oxirane 6 was converted into (–)-GABOB [(R)-4-amino-3-hydroxybutyric acid] 9 (89% e.e.), which is both a neuromodulator of the mammalian central nervous system and a drug.

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