Highly concentrated catalytic asymmetric allylation of ketones

Alfred J. Wooten; Jeung Gon Kim; Patrick J. Walsh

doi:10.1021/ol062264h

Highly concentrated catalytic asymmetric allylation of ketones

Alfred J. Wooten
, Jeung Gon Kim
, Patrick J. Walsh^*

^*Corresponding author for this work

Department of Chemistry

University of Pennsylvania

Research output: Contribution to journal › Journal article › peer-review

60 Scopus citations

Abstract

We report the catalytic asymmetric allylatlon of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99%) with high enantiosetectivrties (79-95%). The resulting homoallylic alcohols can also be epoxldized in situ using tert-birtyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87%).

Original language	English
Pages (from-to)	381-384
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	3
DOIs	https://doi.org/10.1021/ol062264h
State	Published - 2007.02.1

Access to Document

10.1021/ol062264h

Cite this

@article{2a2389b7753a41e7b9fee9207e1f4eec,

title = "Highly concentrated catalytic asymmetric allylation of ketones",

abstract = "We report the catalytic asymmetric allylatlon of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99\%) with high enantiosetectivrties (79-95\%). The resulting homoallylic alcohols can also be epoxldized in situ using tert-birtyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87\%).",

author = "Wooten, \{Alfred J.\} and Kim, \{Jeung Gon\} and Walsh, \{Patrick J.\}",

year = "2007",

month = feb,

day = "1",

doi = "10.1021/ol062264h",

language = "English",

volume = "9",

pages = "381--384",

journal = "Organic Letters",

issn = "1523-7060",

number = "3",

}

TY - JOUR

T1 - Highly concentrated catalytic asymmetric allylation of ketones

AU - Wooten, Alfred J.

AU - Kim, Jeung Gon

AU - Walsh, Patrick J.

PY - 2007/2/1

Y1 - 2007/2/1

N2 - We report the catalytic asymmetric allylatlon of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99%) with high enantiosetectivrties (79-95%). The resulting homoallylic alcohols can also be epoxldized in situ using tert-birtyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87%).

AB - We report the catalytic asymmetric allylatlon of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99%) with high enantiosetectivrties (79-95%). The resulting homoallylic alcohols can also be epoxldized in situ using tert-birtyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87%).

UR - https://www.scopus.com/pages/publications/33847055102

U2 - 10.1021/ol062264h

DO - 10.1021/ol062264h

M3 - Journal article

C2 - 17249767

AN - SCOPUS:33847055102

SN - 1523-7060

VL - 9

SP - 381

EP - 384

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Highly concentrated catalytic asymmetric allylation of ketones

Abstract

Access to Document

Other files and links

Fingerprint

Cite this