Confirmation of the stereochemistry of spiroviolene

• Yao Kong,
• Yuanning Liu,
• Kaibiao Wang,
• Tao Wang,
• Chen Wang,
• Ben Ai,
• Hongli Jia,
• Guohui Pan,
• Min Yin and
• Zhengren Xu

Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77

• BH3·THF in THF, and heated at 60 °C for 3 days. After oxidative treatment of the resultant alkylborane products with NaOH/H2O2, we have obtained three derivatives 9–11 with one hydroxy group in 37%, 30% and 21% isolated yield, respectively, as well as recovery of 10% of the starting material. After

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

• Thiago S. Silva and
• Fernando Coelho

Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112

• nucleophilic species, such as alkyl Grignard, alkyl zinc, and alkylborane species, can be found in the literature [105][106]. A common drawback of these Ni cross-coupling methodologies is the use of nucleophile partners with a low tolerance to other functional groups present in the substrate, as is the low

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

• Anna Kmieciak and
• Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

• borane–dimethyl sulfide adduct in THF at 50 ºC. Oxidation of the alkylborane with mCPBA gave the desired alcohol 27 in 51% overall yield. Finally, diastereomeric endocyclic allylic alcohols 16 and 18 were treated with chlorodiphenylphosphine in the presence of DMAP to produce diphenylphosphinites 28 and

Recent advances in copper-catalyzed asymmetric coupling reactions

• Fengtao Zhou and
• Qian Cai

Beilstein J. Org. Chem. 2015, 11, 2600–2615, doi:10.3762/bjoc.11.280

• primary allyl chlorides to react with alkylborane (alkyl-9-BBN) for the generation of a quaternary carbon stereogenic center bearing three sp3-alkyl groups and a vinyl group with an ee up to 90% (Scheme 29). Cu-catalyzed enantioselective allylic substitutions with Grignard reagents Transition metal

Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates

• Takamichi Wakamatsu,
• Kazunori Nagao,
• Hirohisa Ohmiya and
• Masaya Sawamura

Beilstein J. Org. Chem. 2015, 11, 2444–2450, doi:10.3762/bjoc.11.265

• . Keywords: alkylborane; alkynoate; conjugate addition; copper; multisubstituted alkene; Introduction Copper-mediated conjugate additions of organometallic reagents to alkynoates are powerful tools for the synthesis of multisubstituted alkenes [1][2][3][4][5][6][7][8]. Because of their broad availability

• mode. The syn stereoselectivity was excellent regardless of the substrate structure, and a variety of functional groups were tolerated in both the alkylborane and the alkynoate. Results and Discussion Alkylborane 2a (0.275 mmol), which was obtained via hydroboration of styrene (1a) with the 9

• ). The data in Table 2 show the variety of functional groups attached to alkylboranes 2 that are tolerated in the reaction. The rather crowded alkylborane 2c, which was prepared from tertiary alkyl substituted terminal alkene 1c, reacted nicely (Table 2, entry 2). β-Branched alkylborane 2e, prepared from

Part 2. Mechanistic aspects of the reduction of S-alkyl- thionocarbonates in the presence of triethylborane and air

• Florent Allais,
• Jean Boivin and
• Van Tai Nguyen

Beilstein J. Org. Chem. 2007, 3, No. 46, doi:10.1186/1860-5397-3-46

• plurality of mechanisms.[3] The reactivity of the combination alkylborane/air/water touches many other domains and certainly deserves further study. Xanthates 1a, 2a and their corresponding alkanes. Deuterated O-ethyl-S-ethyl dithiocarbonates 3–5, deuterated adduct 1d and alkane 1e. Kinetics of the